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. πŸ™‚


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. πŸ˜‚

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.” πŸ™„

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 πŸ˜ƒ 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 πŸ˜ƒ


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 πŸ™‚

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 πŸ˜ƒ ) 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 πŸ˜ƒ “. “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 πŸ™‚

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. πŸ˜‰ 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 πŸ™‚

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.” πŸ€”

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 πŸ˜‰

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 vlogΒ 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 πŸ˜ƒ )

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!Β