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

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

*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

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.

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

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.

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

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)

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

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€”

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

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.”

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…

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?


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)

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!

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 …)

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.

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 


    • Jessie says:

      Awesome, I’m glad you like it! I was worried it *might* be a little too long that way, but I think it’s funny to see how we both were freaking out in different ways.

  1. liz says:

    FINALLY! I had gathered that you guys met on IG but this is such a cute story! I so remember mine and Jon’s first kiss! On a cot in x-ray in Iraq (he was an x-ray tech there and I was just hanging out that night). He got a call that a trauma was coming in on the radio so he had to go to the ER and he was like, “Ok I’m finally going to kiss you” and then he did. I was laying on the cot and he was just like, standing above me. Haha. I can’t wait to read parts 2 and 3!!!! Also, I LOLed at Ben’s dick pick part. Those are the worst.

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