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

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. 😂

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

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.

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

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.

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.

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 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!

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.


  1. liz says:

    Um, I’m curious now how the first weekend with a boyfriend who you’d only met a few times went when you were staying with him, haha! FOLLOW UP POST! Also, I LOVED how you set this up. It’s so funny how you remember things different (I LOLed in your Part 2 about how you didn’t really remember the hotel part and he said you just raced right in, haha). I think when you guys are old and married, it’ll be so fun to go back and read this post. I wish Jon and I had done things like this! Love your story! So cute!

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