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

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 …

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

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.”


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.

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.

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 🙂

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.

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


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