Jessie & Ben: How We Met (Part 3)

And it’s officially time for Part 3! If you haven’t already, make sure you didn’t miss Part 1 & Part 2. There are also videos at the bottom of this post because Ben and I did the Boyfriend Tag – I’m all about ALL THE CONTENT this weekend, apparently. 🙂


Who doesn't love a good love story? Here's Part 3 of How Ben & I Met on Instagram! | Jessie & Ben: How We Met (Part 3)
October 2016

Jessie:
We talked a LOT more during this time. I remember freaking out for about a week that I never got an answer from Ben about coming to a wedding with me, so I finally asked him in a text one night. Since the wedding was over Thanksgiving, he told me he’d talk to his family over the weekend and let me know. I didn’t hear much from him over the weekend, and finally on Sunday night he told me he’d call me on Monday so we could talk about the wedding. We talked that Monday and he told me he’d love to come, so we chatted about plans for that.

I also remember my friend Lindsay helping me text Ben one weekend after this because I was FREAKING OUT again that he just saw me as a friend. So she basically helped me be SUPER flirtatious with him via text and I’d make her read it every time he responded because I was so nervous. I basically was a ball of nerves all of late 2016. 😂

Ben:
Despite my slight misstep of not explicitly showing her how I felt after that trip, we ended up talking a lot. I’m not positive, but I think that ever since that day, we’ve talked every day since. Jessie officially asked me to that wedding that she had mentioned the one night she was in Chicago. I told her I’d get back to her because it was the weekend after Thanksgiving so I just wanted to make sure “I didn’t have any family stuff going on.” I was also very nervous about going to a wedding with someone that I wasn’t dating. What were we anyways? It was obvious that we liked each other a lot, but we still lived far away from each other… It seems dumb in hindsight but I just had a lot going on in my brain at this point (I had been single for 6 years…) Anyways, I told her I’d call her to discuss (figured it would be good to start talking and not just texting) and we got everything squared away for the wedding.

Early November 2016

Jessie:
November was a crazy travel month for me with my events job, so I was a little pre-occupied (thankfully). I had a week of events in the Chicago-area from November 15-18. Since that was a Tuesday-Friday, I wanted to find a way to stay in Chicago for the weekend, but I was broke AF. I was talking to Ben about it and he offered up letting me stay at his place, which I thought was amazing, but also terrifying at the same time.

Ben:
Jessie had another work thing going on mid-November. It was Wednesday-Friday, so it was a no-brainer for her to spend the rest of the weekend once she was here. Chicago isn’t cheap and I knew she’d be concerned about spending too much, so I offered that she could stay at my place. We had talked enough by now that I wasn’t worried about this coming off as too forward and was actually hoping that it would be a sign that I was serious about spending designated time with her (I even offered to help her pay for a hotel stay if she wasn’t comfortable staying with me – she was NOT leaving Chicago – and me – to go back to Green Bay on a Friday evening.)

Nov. 15-18, 2016

Jessie:
I remember packing about 17000 things in my bag not sure what I’d need for events or staying at Ben’s. You know what I freaked out the most about? PAJAMAS. I had never slept in a bed with him (obviously). I made my sister shop with me for like a week and I still didn’t end up finding anything “cute, but not trying to hard.” 🙄

On the 15th, I had my only event downtown, but we were staying WAY out in a western suburb and I didn’t have a vehicle. I was chatting with Ben all day and he ended up coming allllll the way out to my hotel that night, just to see me for a little bit. It was SO nice, especially because he works super early in the morning so to have to drive that far out, then back into the city was crazy.

We continued to chat the rest of the week, but I didn’t see him at all. On Friday the 18th, my boss was getting ready to drop me off at Ben’s and suddenly had 10000 questions about him. “Will you be safe?” “Do you know what his roommate is like?” “Is he your boyfriend?” I told Ben all about it (making sure to sneak the “Is he your boyfriend” comment in there…) as we were getting to his place. I remember being SO NERVOUS (again, story of my life). He looked cool as a cucumber though.

Ben:
Going into this weekend, the plan was to just see Jessie on Friday when she got done with her event stuff for the week. We were both done working pretty late in the evening and she was staying about 30 miles out in the suburbs (thanks for nothing Jessie’s boss!) However, once we started texting back and forth that Wednesday that she got into town, all I could think was – SHE’S HERE. In Chicago. Not far from me. Screw it, what the hell was I thinking, I’m not waiting TWO MORE DAYS to see her. So I drove out to the suburbs that night to see her. The butterflies were insane this time around! It was definitely the right choice though – there’s no way I would have been able to fall asleep that night knowing she was within an hour of me.

That was the only time I saw her before Friday afternoon. We both had a bunch going on and it just didn’t work out. No matter, I got her alllll to myself come Friday afternoon 😃 Her boss had to drop her off because they had driven in together. On the way to my place, she was texting me telling me all these questions her boss was asking her. One of those questions was, “Is he your boyfriend?” I knew at that moment, that was going to be my in to “officially” ask her to be my girlfriend. I laughed it off over text and waited to revisit it for when we were together in person.

She finally arrived (I swear I was like pacing and cleaning my place for the whole hour or whatever it was that she was in the car lol.) I was so excited to finally have her there with me and so nervous to ask her the “girlfriend” question.

Jessie:
And then … Ben sat on the couch with me and I was kind of leaning back on him. We were chatting about my week and what we were doing that night with his friends. (I was meeting his friends that night and then his dad and sister on Saturday. Talk about throwing me into the weeds!) All of a sudden he brought up the conversation with my boss, and I froze. I remember getting SUPER hot (like sweaty hot LOL #sexy) and wouldn’t look at him (thankfully I was leaning back on him). We were laughing about my boss being nosey and then Ben was like, “what if I was your boyfriend?”

I FROZE.

I don’t even remember actually answering. I think I awkwardly said something like, “that would be nice” or something. He ended up having to ask me again (I think) because he didn’t know what my answer was HA!

Ben:
After I showed her the place and everything, we sat down and started talking. We were going over plans for later, asking about each other’s days… and eventually I brought her boss’ question back up. We laughed and then I said, “Well what if I was your boyfriend?”

*Jessie awkwardly laughs, blushes, and stares at me for what seems to be 5 minutes*

“Well…. ” I say slightly panicked, “do you want to be my girlfriend or not?”

She laughed again and said yes. What a perfectly awkward ending to our pre-relationship relationship 😃


And that is the story of how I met my boyfriend on Instagram and somehow convinced him to stay with me this past year. It’s been the best year of my life and I’m so grateful to have him. ❤️

And if you just CAN’T GET ENOUGH, make sure to check out our Boyfriend Tag videos on YouTube.

Jessie & Ben: How We Met (Part 2)

And we’re back with Part 2! If you haven’t already read Part 1, make sure to check it out.

So, where did we leave off? Oh yes … the first date. Fast forward a bit to the next few steps in our relationship!


Who doesn't love a good love story? Here's Part 2 of How Ben & I Met on Instagram! | Jessie & Ben: How We Met (Part 2)
September – Early October 2016

Jessie:
I remember talking with him WAY more frequently, but I was so confused. He was rarely flirtatious (at least in the way I was used to), but he texted me or snapped me every day. And he always at LEAST liked one my Instagram pics, if not commented. He remembered little things I told him, would send me pics of the sunrise or something about Harry Potter or songs I liked. Quite honestly, re-writing this now, I have no idea why I was convinced he just liked me as a friend.

I decided earlier in September that I wanted to take a solo-trip outside of work to really take some time to figure out what I wanted. Initially I was thinking of going somewhere crazy like California or Colorado, but then decided that was a bit out of my price range (and comfort zone) and decided to go to Chicago instead. I loved the city and loved visiting there for work, but figured it’d be fun to go on a “me” trip there. Plus, maybe I’d get to see a cute Chicago boy …

Ben:
As great as meeting each other was, I really didn’t any thought to “dating” Jessie right after that. We lived 4 hours away from each other and that was where my thought process stopped. I DID however, definitely want to see her again and knew there was no way in hell I was waiting until mid-November until her next work trip.

We did talk quite a bit more after this. Luckily for me, she soon mentioned that she was thinking about taking a long weekend in Chicago in October. I was already planning on asking her to come down for a weekend but was in the process of figuring out how I wanted to pose that question. Between “hey how about you make the 8 hour round trip to me again” and “well you can stay with me and I’ll sleep on the couch” I was definitely nervous about asking. Thank god she really wanted to see me again too 🙂

October 10-12, 2016

Jessie:
ME TRIP! That I filled with 1000 things to do and people to see LOL. Of course, the first person I reached out to was Ben, then Marette, haha. Since I was coming on a Monday-Wednesday, Ben had to train clients at night, so we decided to meet up for drinks late on Monday night. If you’d like a whole vlog on my Chicago trip, you can check that out here (INSERT VLOG HERE)

I had so much fun in my cool hotel room and got ready for dinner with Marette that night. Marette has basically seen my entire “love story” unfold! We had dinner at Happy Camper and then I went back to my hotel to wait for Ben to get done training. He had told me he was going to take me to a surprise place and he’d pick me up from my hotel. I remember being SO giddy, just being in Chicago and getting to see him again, even though I was hella nervous. I tried on about a zillion outfits and sent pics to my friends Lindsay and Amy before heading out to meet him downstairs. There was that big smile again…

Ben ended up taking me to Cindy’s Rooftop Bar because he knew I’d love the view of the city at night – HOW SWEET IS THAT. I was in complete awe standing outside looking at the pretty city (and pretty boy, hello). We literally got one drink each and ended up finding a table and talking for hours. I remember the Cubs were in the World Series so that was on TV and we were literally the only people in the entire place NOT watching the game.

We had CRAZY in-depth convos about everything – from kids to cheating to future dreams and plans. I remember him saying he really wanted kids and that was almost more important to him than getting married, and that totally threw me off. I had always been the opposite – knew I wanted to get married, but wasn’t so sure on the kids. (This ended up being a fun conversation we had on our trip to South Carolina a few months later when we both were confused about what the other said – haha! If you want to have crazy talks with someone you’re dating, go on a road trip together.)

He walked me back to my hotel and we sort of hugged in the lobby of the hotel. I think he kissed me? I honestly don’t remember, I was so nervous! I wanted to bring him up to my room to hang out, but I didn’t want to give him the wrong impression that I wanted “more than that” – because I didn’t. I wanted to take things extremely slow. So our good-bye was awkward and I immediately texted him apologizing for not asking him up. He said something about a funny Uber driver and said, “I’ll have to tell you a story about it tomorrow, if you’ll see me again.”

WOOHOO HE WANTED TO SEE ME AGAIN!

Ben:
Finallyyy she was back. I was super excited to see her again. She was coming in from a Monday-Wednesday, so we weren’t going to get to spend big chunks of time together and do typical weekend city stuff. We settled on drinks after I was done training clients that Monday evening. I decided to take her to Cindy’s Rooftop – it was a touristy, yet classy, cocktail bar that is known for its views of the city at night. (Editor’s Note: Ben wrote in “insert link” by Cindy’s Rooftop and that’s how you know he’s a good #BloggerBoyfriend)


(Photo cred^^)

It ended up being the perfect spot (it was very mild for Chicago in October) and we talked for a few hours. (So much for not spending big chunks of time together 😃 ) We talked about anything and everything – seriously… there wasn’t really a topic that was off the table. It was amazing. All I’d ever wanted when dating was being comfortable to be 100% open. This was that and more because she clearly felt the same way. It was that night that I knew we had a future – there were the beginnings of a deep connection there.

Once again, we had talked past midnight on a “school night” for me. (As a personal trainer, I regularly have clients at 7am or earlier so this was way past my bedtime #worthit) We left and walked back to her hotel. The nerves set in really hard again – we just had a great night of chatting – now what… *Disclaimer! I had no intention on “going up to her room”. It was late AF and quite frankly, the night had been amazing. I wanted to take things slowly and was more than happy with how the night had gone.

As we approached the entrance to her hotel, I slowed down, anticipating she was going to do the same – bid me farewell, share a kiss (after the first date debacle), and both go off dreamy-eyed into the night. NOPE. Jessie just powered on ahead, right through the doors without looking back or saying a word. Suuuper confused, I followed her in. The hotel had a massive lobby and Jessie just continued towards the elevators without giving me any sign of what was going on. At this point, my thought process looked something like this…

What the hell is she doing… why is she not giving me any cues whatsoever… it’s rather assuming of her to just expect me to follow her up to her room without saying anything… I’m really effing tired…

… “Okay, well it was great to see you again. Have a nice rest of your night okay?” I cut in and ended the evening. We shared a brief, extremely awkward, kiss and I turned and walked out as confused as ever.

This time I really didn’t know what to think. How could two people connect so genuinely through conversation and then be a complete mess when it came to showing what seemed to be obvious affection. Was it too early? Were we both just a bit tentative/confused?

My Uber driver arrived – a large, outspoken black woman – I jumped in, and she asked if I had seen the Cubs World Series game that just happened. I told her no, because I was on a date and it went really well so I wasn’t paying attention. She said “ohhh, so that’s why you were just coming from the hotel then huh?”. I replied yes, but probably not in way that she assumed – I had just dropped the fine young lady off. She proceeded to berate me and ask how the hell I could just leave a nice young lady to go back to her room all by herself. I can assure you that this was MUCH more drawn out and explicit – which I actually found hilarious. A few minutes into the ride, Jessie texted me apologizing for our awkward parting but that she was totally conflicted about what to do at the moment and just froze. I felt much better to hear this and I told her that I had a great story (Uber driver) to tell her, “so I guess we’ll have to hang out tomorrow 😃 “. “Perfect” transition into hanging out again.

Jessie:
The next morning I slept in and then went to coffee (for like, three hours) with my friend Laura before heading to lunch by myself. Ben texted me while I was with Laura to formally ask me on another date and I was freaking out. I had actually set up a date with a different Ben (ha…) for that night a few weeks prior that I had met through the college I worked at. I wanted to see MY Ben, but I felt bad canceling with the other Ben. Laura was like, “Which one do you actually want to see?” Obviously I said Ben F, so she’s like, “Okay, there’s your answer” so I canceled on the other Ben. Whoops.

I did a little shopping, then headed back to my hotel to get ready for dinner with my friend Amanda. After drinks and dinner, I walked to meet Ben at a restaurant near his work that happened to be near where I had dinner with Amanda. He was eating when I got there (since I had already eaten) so after he was done, we walked to Broken Shaker to get another drink. We ended up having even longer conversation than the night before, much more flirtatious (woo!) and he walked me back to my hotel.

Ben:
Even though we ended the previous night “agreeing” to see each other again, I wanted to formally ask Jessie out again that night. I knew she was only in town for a few days and as much as I wanted to see her, it was HER vacation. She agreed (wooooo).

We ended up going back to the Broken Shaker again because we liked it so much the first time around. We were able to break some of the awkward tension with my story from the night prior and got in yet another longgg conversation. Jessie even managed to half-ass invite me to a wedding with her in Green Bay for a month later. I figured she was fishing buttt I managed to avoid it (not really even sure why…) and the conversation continued. Hours later, I walked her back to her hotel… and finally got the not-awkward goodnight kiss I had been waiting for 🙂

Jessie:
The next morning I was SO nervous. Now I knew for sure I had feelings for this guy, and I was so afraid he didn’t feel the same. He barely texted me that day so my nerves just increased more and more. I ended up taking the train back to Milwaukee, then drove home and texted him a bit here and there.

Ben:
I was officially “in love”. However, I knew Jessie was finishing up her trip that day and didn’t want to seem overanxious, so I didn’t text her until late in the day. Whoops…


And that’s Part 2! Stay tuned for Part 3 – and the FINAL version of the “How We Met” story. Thanks for sticking with me. ❤️

Part 1

Jessie & Ben: How We Met (Part 1)

Hey friends and happy Friday! Tomorrow is a pretty spectacular day because:

  1. My friend Heather is getting married and we get to go to Milwaukee to celebrate
  2. It’s Ben and my 1st “Official” anniversary ❤️

Ben and I decided earlier this year that we’d celebrate our anniversary as the first day we met “in real life” (Sept. 1), but I still think it’s a pretty special day. Nov. 18, 2016 – the day Benjamin made me the most happy (and most uncomfortable – I WAS NERVOUS) girl in the world.

So, instead of telling y’all a bazillion reasons why he’s my favorite human, I figured we should FINALLY write about how we met – but from both of our perspectives. 😊  And remember, at the time, I was living in Green Bay and he was in Chicago, so there wasn’t any time for seeing each other in person.

This is Part 1 of 3, because apparently we like to talk about ourselves. 😉 Part 2 will be up Saturday and Part 3 on Sunday!



January 2016

Jessie:
WHOA, CUTE BOY FOLLOWED ME ON INSTAGRAM … must stalk… yep, follow back.

Ben:
*Uses Crowdfire app to mass follow people that follow similar accounts to grow my Instagram. Follows Jessie Deschane by chance without knowing anything about her.*

February 14, 2016

Jessie:
I put up a random picture of me in the gym, saying something about being at the gym on Valentine’s Day and guess who pops up as liking the picture? Cute donut boy again.

Ben:
I liked one of Jessie’s pictures. I wanted to show engagement. But also probably because she was wearing a “Do you even leviosa?” shirt. I don’t think the fact that it was Valentine’s Day had anything to do with it. However, I LOVE weird coincidences and would like to think that it was some crazy foreshadowing about what was to come for us 🙂

Random likes and comments in between February and June; Started following each other on Snapchat at some point.

June 17, 2016

Jessie:
After a run-in with a creep on the road, I went on a LONG Snapchat rant about guys being rude to girls when trying to get their attention. I then started driving to Madison to have a girls’ weekend with my friend Lindsay and when I stopped for gas, I had a Snapchat message from a certain Ben Fritz Fitness – my stomach dropped. He made a funny comment – “What, that’s not how I should be trying to get girls attention?!” and we joked/chatted back and forth for the rest of the night.

Ben:
At this point I was pretty into Snapchat, so I was watching stories all the time. I think I was watching Jessie’s pretty consistently by now; between that and IG, her sense of humor and cleverness definitely had my attention at this point (besides being physically attracted to her.) After hearing her talk about some douchebag who followed her (they were both driving) and try to get her number or something, I thought it would be funny to comment by saying, “Oh… maybe that’s why I’m still single” or something to that effect. Super lame joke? Yes, but it worked – it subtly (not really) put out there that I was single and opened the door to communicating on a more direct basis. THANK YOU SNAPCHAT STORY RESPONSES.

June-July 2016

Jessie:
Snapchats and Instagram likes/comments started to become a little more frequent. I had convinced myself that he was just a nice guy and wasn’t actually interested in me, so I played it off (though I did get butterflies every time I saw a notification from him pop up)

Ben:
I was taking every opportunity I could to make contact with Jessie by now – IG posts, Snap stories, even a couple direct snaps here and there (oh snap! #gettingserious). Definitely felt a connection with her, but didn’t allow myself to think much of it since she lived in Green Bay, WI and I was in Chicago #21stcenturypenpals

July 14, 2016

Jessie:
We were supposed to meet after my event in Chicago, but I ended up getting pulled into a dinner with our donors so I had to cancel with him at the last minute. I didn’t want him to think I was bailing on him, because I truly wasn’t! Because with most guys, I would bail – but remember, I had convinced myself he was “just a friend from Instagram.” 🤔

Ben:
I remember being pretty bummed about this. It was exciting to think that I was going to meet that witty, cute girl from my phone screen in person! But I could tell that she truly wanted to meet up with me at some point and wasn’t just playing some annoying girl/guy game. Someday I’ll meet her…

July – August 2016

Jessie:
Continued with the Snapchats and Instagram comments. Ben was NOT outwardly flirtatious, so I really thought he wasn’t interested in me “that way.” He somehow sneakily got my number, but I don’t remember exactly how. He would occasionally send me snaps while he was driving to work in the morning because he drove right past the sunrises on the lake – BUT AGAIN, HE WAS NOT INTO ME. #SmartGirlBrain

We decided we’d meet up after my event in Chicago on Sept. 1 for a drink. I was again CONVINCED it was just a friendly drink. In fact, I was also meeting my friend Marette who I had never met “in real life.”

Ben:
I specifically remember a turning point of our communications going from casual to more personal. And no, by personal I do not mean dick pics, or even shirtless selfies. *Note: if you’re a guy and you’re sending unsolicited dick pics, fuck you – you’re a pathetic, disrespectful asshole.* As for the shirtless selfies, I was just posting those to my story because I knew that she was watching that 😉

Anyways, turning point… I had discovered that she loved sunrises. I love sunrises as well (they’re magical) and at the time, I was driving along Lake Michigan in the morning at sunrise to get to my clients at the gym. So naturally I thought of her and had to send her a snap. I probably did this a couple of times. One of these days, we somehow continued a conversation and started talking about travel. I was sitting at Starbucks before my first client and was nervous and excited to be having our first “real” back and forth convo – connecting over something that we are both passionate about. At this point, I asked for her number – I could tell that there was chemistry and I knew that she would be in Chicago soon for work so I wanted to make sure I had the most direct line of communication open.

Sept. 1, 2016 – the lead up…

Jessie:
For some reason, I got a little more dressed up this day… but totally for my event, OBVIOUSLY not to impress a boy that wasn’t interested in me even though he texted me/snapped me or liked my Insa pics every day. I remember my friend Brooke totally “momming” me and was freaking out that I was meeting TWO internet strangers after my event, but I was totally all about it. I actually have a vlog from that trip.

Once I got to Chicago, I got through my event and headed off to eat dinner with Marette. We had such a great time and I totally forgot about my phone until I realized I was supposed to be texting Ben and letting him know when I was leaving. CRAP! I remember talking to Marette about how nervous I was even though it was TOTALLY platonic … obviously.

I took a taxi back to my hotel and got ready a little bit before meeting Ben out. I remember specifically putting on more makeup and trying to get myself to stop freaking out because it SO wasn’t a date. I wasn’t dating. So it wasn’t a date. NO. I left a little late (because I was so nervous) and walked the couple of blocks to Broken Shaker. I walked in and saw him standing there and he smiled so much when he saw me. Want to know my first thought?

FUCK IT’S A DATE.

Ben:
I had a fantasy football draft and was getting to meet the sexy girl from Instagram this evening. BOOM – talk about hitting the jackpot. For me, the night really couldn’t be any more perfect. I remember being nervous that Jessie wouldn’t want to meet up because I knew the draft would go until at least 9 or 10 and thought that might too late for her. Luckily, she wanted to meet me as much as I wanted to meet her.

The draft was at the gym that I work at. We ordered a bunch of pizza and beer and it was set up to be a great time. It was a disaster. Okay, not because of how the actual “party” went – it was fun to hang with the guys and have a couple beers and talk football. My draft was a disaster – as in, the players I picked. (“Nobody reading this knows what the hell a draft is Ben!”) THE POINT IS… I don’t think I was focused on the draft nearly as much as I thought I was. I was super excited to meet Jessie, but also nervous. Have you ever met someone in real life that you’ve spoken to for MONTHS via text? Weird.

I don’t drink much and was slightly concerned about the couple of beers that I had. I truly wanted to meet this girl and I didn’t want to be too tipsy or acting awkward acting like I wasn’t tipsy. Confusing I know. But that’s what you do before dates, you overthink things. Either way, the butterflies had set in and it was time to go meet her.

I got to the cocktail spot first. (This was my first time there #risky but luckily it was the perfect environment.) When Jessie walked in, my first thought was “She is short! And… Damn she looks good in that white and black dress from IG!”

Sept. 1, 2016 – The Date (because that’s what it was, Jessie)

Jessie:
I was freaking out. I don’t remember much from the date, to be honest, because I was SO nervous. I remember sitting in a little corner of the bar (super cool place, by the way) and chatting for so long. We never had a pause in conversation and everything just felt super comfortable. We “knew” each other from Instagram and Snapchat and had gotten to know one another that way, so it wasn’t awkward in any way (except for me asking weird-ass questions). I do remember him scooting closer to me a few times, touching my leg and totally brushing my booty at one point (SASS). We had one drink (maybe 2?) and talked the rest of the night.

Ben insisted on walking me back to my hotel even though it was a couple blocks away, but it was pretty late so I appreciated the gesture. We got in front of my hotel and I remember feeling so nervous, so I hugged him real quick. I remember him mumbling something like, “Can I kiss you” and then planted one on me before I could even react. I didn’t even kiss him back!

Ben:
The date was awesome. I think it was awkward for like 2 minutes and then totally relaxed the rest of the time. It was great to “know” her from social and some chatting because it made conversation flow so much better. We were able to talk about things with more substance rather than just your typical first date questions. It was almost weird how un-forced the convo was (relative to other first dates or just meeting other people for the first time in general.) Based on that alone, I knew this was someone that I wanted in my life. (Cheesy much? Look… I’m an introvert and genuinely connect with very few people. Therefore, I can tell when I do and this was one. A beautiful one at that 😃 )

When the date was over, I got nervous. As great as I am in conversation, I’m a terrible “closer”. Before you get too carried away in the gutter… I mean this in every way possible – I just have a hard time smoothly transitioning to whatever comes post-date. As I said above, I knew that I liked her and wanted to make that known. So I walked her back to the hotel she was staying at a couple blocks away. I have no idea what was being said as we stood outside of that hotel door, but apparently I asked her if I could kiss her (who does that?? *facepalm*). I’m pretty sure I didn’t even let her answer and proceeded to kiss her while she just stood there stunned.

Sept. 2, 2016 (technically because it was after midnight …)

Jessie:
I immediately got inside and started freaking out. I couldn’t believe I didn’t kiss him back! Shit! He’s going to think I’m not interested. He texted me a couple minutes later to let me know he got to his car safely and we chatted a bit there, so that made me a bit more comfortable. I think he made a joke about the kiss and I said something like, “I wasn’t prepared!”

I woke up the next morning and was CONVINCED he didn’t like me. (I had/have great self confidence) We texted a bit back and forth, and then I headed back to Green Bay. I remember specifically putting up an Instagram post and tagging him in it, and he didn’t respond the way I thought he would, so I got even MORE nervous that he didn’t like me. Typical.

Ben:
Fackkk, why didn’t she kiss me back?!… things went so well, I thought we were for sure on the same page… ESPECIALLY because I don’t know when I’ll even get to see her again… god I’m awkward, how did I mess that up… ughhh, I guess it doesn’t matter because she lives in Green Bay anyways… *sigh*…


Part 2 coming tomorrow! I hope you guys enjoyed our long-winded first blog post! 

Five Things I’m Loving on Valentine’s Day

Happy Valentine’s Day, friends! Now, I’ve never been one for celebrating a random day in February with or without a boyfriend, BUT I am all about love. So with that, here are five things I’m loving.

5 Things I'm Loving on Valentine's Day

Just Jessie 
Did you know I’ve officially been blogging on here for five years? Crazy! I had a small food + weight loss blog before I started Just Jessie, but I’m so happy I switched over to this one.

I’ve made so many fun connections with new friends and brands in the past five years and I can’t wait to ramp things up this year with making my brand into a business. I’ve decided to finally put my passion and talents to use by providing my own content creation and social media management service. I’m so ready to work hard toward the life that I want!

Chicago
I lovvvvve this city. I love being able to walk to things or get to places easily (I still need to figure out the trains …) I love the energy of the city and how empowered I feel all the time. I mentioned this in my post back in October when I had my solo trip to Chicago, but this city gives me a sense of excitement and the push to go after everything that I want. I still can’t believe I live here and I’m doing it. I’M DOING IT, GUYS!

Warmer Weather
The weather has been sneakily warming up. Granted, it’ll be 50 one day, then 27 the next BUT IT’S STARTING. Everyone keeps telling me that Chicago is amazing in the summer, and I’m ready to see what that’s all about. Plus, dresses without tights?! I do need to do some spring/summer clothing shopping and shoes shopping, but I’m going to wait until I’ve hit a few goals with my fitness journey.

Friends
New and old, I love that I’m able to be around fun people more often. I’ve hung out with more people since I’ve moved to Chicago than I did the entire 2.5 years I lived in De Pere. I’m joking, only sort of. I’m pretty sure it’s close!

Ben
I mean, I can’t do a Valentine’s Day post and NOT mention him, can I? 🙂

After being single for over four years, having someone in my life has been a challenge, but a good one. He’s smart, kind, loving, funny and I didn’t know someone like him even existed. But he does and I’m not sharing. 😛

Plus, he feeds me cake and donuts, but also pushes me in the gym. Best case scenario in my opinion.

What are you loving right now?
Are you doing anything for Valentine’s Day or Galentine’s Day or Single’s Awareness Day OR JUST FEBRUARY 14?

Weekend Recap: A Sleepy NYE in Chicago

Happy New Year, friends! I hope you’ve had a wonderful weekend and rang in the New Year in whatever style works for you.

Ben and I got home from our road trip (recaps of that coming the rest of this week!) late on Friday night, so we slept in a bit on Saturday which was AMAZING. Once we finally got up, we headed out to the suburbs to pick up Ben’s car from his parents’ house and then headed back into the city where we didn’t move from the couch the rest of the day. SO lazy.

After some Thai takeout (yum), we got ready to head out to Ben’s cousin’s place for a fun night of hanging out with lots of fun people. We had a couple of drinks, stuck around for the NYE countdown at midnight and then headed up to the rooftop of the building. Got a picture with my man … 🙂

chicago NYE

And then we headed back to Ben’s place to go to bed because we’re old and tired.

Now it’s Sunday and I’m currently sitting at Starbucks with Ben, writing this post while he gets some work done. My gym job and social media job are officially done (woo!) so I’m just focusing on the last few days of work this week at the college and then back to Chicago next weekend except PERMANENTLY. I’ll head back to Green Bay later this evening and then I’ll be figuring stuff out this week. I can’t believe 2017 is here – time for some BIG changes, friends!

I’ll have 3-4 posts about my road trip with Ben coming up this week as well as a requested story of how Ben and I met (thanks, Liz!) soon, too. I’ll also keep you all updated on the move and all the craziness (good and bad!) that come with it. I’m so excited to get back into blogging and vlogging – the things I’m passionate about have taken the backseat the past few months due to so much craziness with my three jobs. I hope you’ll stick around for the ride. 🙂

How was your NYE? Did you do anything fun or were you pretty low-key?  

Linking up with Katie!

New Hair & Wedding Dress HELP

Happy Tuesday, everyone! Tuesdays are always the hardest day of the week for me, for some reason. Usually I’m running on pure adrenaline on Mondays, but by Tuesday, I have to physically push myself out of bed. But I’m here!

Anyways, I got in a spur of the moment hair cut / color last night and … it took 3.5 hours. My hair just pulls yellow like nobody’s business! So a million years of toning later …

Before and After

It’s horrible lighting, but basically it’s a lot darker, with less warmth and more cool blonde. The bottoms are pretty much gray right now, but that’ll wash out and be an ashy blonde. I like it, but it always takes me a little bit to get used to change to my hair – I’m very particular about it!  But most of all, it needed to be cut SO badly – the split ends were out of this world!

Moving on from that, I wrote about my weekend yesterday, but as always, gotta plug the YouTube video. It’s short (what, me do a short video?!) and is just my day on Saturday for Homecoming if you’re interested in watching!

Okay, last but certainly not least … I NEED HELP. I have two dresses (albiet they’re basically the same damn dress …) that I need to choose between for a wedding next month. Normally, I would not care, but for the first time in about, oh, I don’t know … eleventy billion years, I’m actually going to have a date to a wedding (#shocker) so yo girl needs to look spiffy. Which do you prefer?

Dress - which to choose!

And last but CERTAINLY not least, it’s my BESTEST LOVE’S 30th birthday today! <3 Love you, Amy!

Amy's birthday

What is your least favorite day of the week? Favorite day?

“Tutu

Let’s have coffee

I love these types of posts. Whether it’s coffee, tea, diet code red mountain dew (my teeth are going to rot off, I swear) … I love getting coffee with a friend and catching up. Since I don’t have many in-person coffee dates planned, let’s have one together!

Coffee Date

If we were having coffee …

I’d tell you about the awesome, life-changing and uplifting trip I had to Chicago last week. Do any of you ever just “click” with someone, something, some place? That’s how I felt with Chicago. I’ve always liked it there, but this last time just solidified things for me. Even a few of you who watched my video noticed how happy I was, which is crazy to me that you can see that!

I’d ask you a million and one questions, because that’s what I do. I love hearing about things happening in my friends lives, whether it’s how passionate they are about their work, a new person joining their family, a funny date story … I love it. So how about you tell me something about you in the comments? I’d love to hear it. 🙂

I’d probably spill some of my drink on myself, let’s be real.

I’d tell you about a huge weight being lifted off my shoulders. After over a year of being denied by loan refinancing companies, one finally refinanced my loan based on my credit score instead of solely based on my very low salary. So, my payments were supposed to go up to $867 in January (per month) … and the loan refinancing company cut that in half. It’s a HUGE weight off my shoulders and a little more manageable. Seriously, check out SoFi if you’re struggling with student loans (or any type of personal debt).

You’d probably ask me about my dating life because, well … that’s what people ask single people. It’s okay, though. I’m used to it. I’d tell you I’m not actively seeking anyone, not online dating, none of that. I’d tell you that I’ve given up on the dating scene where I live a long time ago because I have no intention of staying in the area forever, which obviously hinders my dating life. Now, if you prod a little bit more, I’d probably tell you about someone that currently has my “attention”, so to speak, but I’m nervous about it. Girl has been burned quite a few times, so I am apprehensive. But you would be able to see past the nervousness and see that I’m more excited than nervous. We’ll see what happens. 🙂 (<— I’m THE BEST at being vague enough that ya’ll will hate me)

I’d ask you your opinion on what to wear for a wedding next month because girl is BAD at making decisions.

I’d ask you about your favorite hair stylist … hair is a big deal for me and I haven’t had mine done in almost a year. Whoops …

I’d tell you about how crazy my November is going to be for work – just the full-time job. I have five events next month, but four of them require overnight travel. Nov. 3: Madison, Nov. 10: Minneapolis (overnight), Nov. 15-18: Chicago (multiple overnights). I’d tell you that I’m excited about it, because getting out of the office and being at my events is the best feeling. Although, you would probably be able to tell that I’m hopeful for new opportunities soon.

I’d tell you that we need to have coffee more often because I miss being with like-minded, fun, energetic, driven people. So, I’d basically beg you to be my friend all the time. 😉

Linking up with Amanda!

I asked you above, but if we were getting coffee, what would you want to talk about? What would you ask me? What kind of drink would you get?

10 Things Single Girls Hate Hearing

I have a lot of experience on this topic of singledom and after going stag to yet another wedding this past weekend, I figured it was time I named off 10 of the things I’m TOTALLY over hearing since I’ve been single. (Note: I’m not being mean and I’ve probably said all of these things myself to someone, but I’ve heard these things about 10,000 times in the past three years.)

Are you seeing anyone?

I’m seeing you, being all judgmental and asking me AGAIN if I’m seeing someone. Don’t you think I would’ve TOLD YOU THAT?!

He’ll come when you’re not looking

First, and most importantly … that’s what she said. #tyss
Okay. Seriously? I’m not sitting on the side of the street with a sign that says “WILL YOU BE MY BOYFRIEND??!!” I’m not going to the grocery store and attacking every male I see. This comment drives me nuts. YES, I get what people actually mean by it, but I haven’t been “looking” for someone, so knock it off.

Things Single Girls Hate Hearing

Have you tried online dating?

Yes, I have. Have you seen my video about my creepy dates? Now you’ll see why I’m no longer doing online dating. (P.S. ignore the quality, I need to re-do this video)

Have you met my friend/coworker/trainer/brother’s friend’s neighbor’s dog walker?

No, I haven’t. And I no longer trust your judgement after you tried to set me up with the waiter at the last three restaurants I’ve been to with you, so you can just stop trying to help now.

Things Single Girls Hate Hearing

So … you’ve at least been getting laid, right?

……………………………………………………………………….

Things Single Girls Hate Hearing

Don’t you want kids? You’re almost 30!

I want a dog. Do I have to get a boyfriend to have a dog? Didn’t think so. Also, I AM NOT ALMOST 30 SO SHUT YOUR DIRTY MOUTH. No offense to my 30s crew! 🙂

Things Single Girls Hate Hearing

You’re so lucky to have this time to work on you.

I don’t need anymore work, thank you very much. Wait, why do you think there’s something I need to work on? What’s wrong with me now?!

Things Single Girls Hate Hearing

Ugh, this must be so hard for you.

Girl, I’m single, not dying of an incurable disease.

Things Single Girls Hate Hearing

Everything happens for a reason. 

I mean, I believe this one for most things in life but I’m soooooooooooo sick of hearing it. Yes, I know. now.please.stop.saying.it.to.me.

Things Single Girls Hate Hearing

I can’t believe you’re still single, you’re so awesome and beautiful and wonderful!

I tell myself this one all the time, so I don’t mind this one. #ProbablyWhyI’mSingle

Things Single Girls Hate Hearing

Do you have any to add?

Linking up with Amanda!!

Being single is hard

Okay. Here we go. It’s rant time, I apologize.

Being single is hard

^^ This. This is something I’m okay with about 95% of the time. I’m okay with being alone. I’m okay with not being in an unhappy relationship anymore. I’m okay with not letting guys treat me like crap. I’m all good with that. I like who I am, I like (for the most part) what I’ve done with my life. I like my goals, my aspirations, my dreams. I’m more worried about when I can get a dog than when I can have babies. In fact, I don’t even think I want babies (that’s a rant for another day). I’m not afraid of living by myself. I have no issues going to movies or getting food by myself. But you know what? Being single is still hard.

It’s still a sting to your confidence when a guy you liked for months but “wasn’t ready to date” suddenly has a girlfriend. Or when your ex of millions of light-years ago is engaged to the crazy chick you always knew in the back of your mind was interested in him. Or when the guy you’re not even interested in gives up on you and moves on … How does that one make sense?

Single

I’ve been the girl that’s told other people that “it’ll come when it’s right” or “at least you’re not in an unhappy relationship” or “you have to like yourself first”. And I believe ALL those things. But being single is still hard when you don’t want to be single anymore.

Now, take that with a grain of salt. One thing I’m really good at is dealing with hard situations (#TWSS). As much as it gets me down sometimes and I feel really lonely (which is actually more of a job/friend/location issue than guys), I’m still gettin’ along. I’m happy by myself. I’m happy with who I am. I mean, I wish I made a bit more money so I could wear prettier clothes (let’s be honest), but I know who I am and what I want. And honestly? I think that’s why I’m still single. I’ve had multiple opportunities to be UNsingle in the past three years, but I strayed away from them because 1) I wasn’t ready yet or 2) I just didn’t “feel it”. So really, it’s my own fault. But I’d rather be single than with someone I’m not 100% into.

Single

So anyways, this little rant is just all over the place but I was having a rough morning after seeing a fun picture on the FaceSpace (seriously, I should just delete certain people). But let’s be real – there’s no use in feeling bad today because I can still do this …

Single

So maybe I should stay single anyway. 🙂

Thanks for listening (are you really listening? reading? laughing at me?) to my little cranky funk this morning! Let me know if you’ve ever struggled with this stuff! Even you beauties that aren’t single, I’m sure you have some advice … but I swear if one more person tells me “everything happens for a reason” … >:( (just kidding)

Linking up with Amanda!