CherryPick logo

A Multimedia Story by Jill Marbach

V. Log Out and Meet People

I decided to go more general this time around and joined the dog lovers bunch. As expected, there were tons of men showing off their best photos with their canine companions. After a while, I found myself more focused on the dogs than the dudes. What can I say? There were some cute ones.

After making a few matches there, I switched gears to a very different one, anxiety even when nothing is happening. There, I felt myself becoming less critical of the guys I was looking at because it felt like we had already revealed something personal to one another. Sadly, I ran through all the options on there in a short amount of time. I guess guys with anxiety aren’t CherryPick’s largest population. Still, I ended up with a handful more matches to talk to and a couple that were actually kind of cool.

All of that only left one more step: actually meet up with some of them. Obviously, I knew that that was the whole point of dating apps. They were a place to meet people so that you could see if you connected in real life. I was totally on board with that. I knew I would never really fall for someone I didn’t know, but the act of getting to know them was foreboding.

First of all, you have to pop the question. When is the right time to ask someone out? How long does it take to be sure he’s not a creep? Then you have to worry about what he’ll say. If he does agree, what sort of thing do you do with a guy you’ve never met? Do you go the traditional route, dinner and a movie? That’s a lot of time to commit to someone you might not click with. There were more informal dates, like getting coffee or walking through a park. Those didn’t really leave you much to do, though. Can you ask different guys to the same coffee shop, or will the regulars start to catch on to what you’re doing? Do we each pay for ourselves? When is the right time to call it if you're not vibing with someone? I’d heard people recommend going on at least two dates with the person before writing them off to get past the initial nerves. That felt like a lot of wasted time if it blew up. If things go well, is a kiss goodbye appropriate? How about just holding hands? When should you ask them on a second date?


There were too many unknowns when it came to going on actual dates, so I was not eager to jump into it. Some of my matches, however, had different ideas.

Eli asked me out first. Specifically, he asked, “Would going to the Magic Gardens count as a novel first date?”

I could appreciate his callback to my bio, and I was intrigued by the offer. Philly’s Magic Gardens was an outdoor art exhibit filled with cool sculptures and art pieces. It was, in my mind, an awesome and novel first date idea. I told Eli that, and soon enough we made plans to go.

Despite all of my anxiety about going out on an actual date, Eli seemed promising. He wasn’t a creep or a fuckboy, and, on CherryPick, we managed to uphold a conversation. This date looked like it was going to go well.

The only problem was you can’t measure chemistry over a dating app.

The entire date was fine. We chatted about Broadway a little bit and what we were majoring in, and we even shared some jokes about the art we were looking at. That was about the extent of our connection, though. Eli really did seem cool, but it was obvious from the start that there was nothing between us. The date had plenty of long stretches of silence, conversations that just didn’t get off the ground, and ended with only niceties.

“See ya around!” Eli said as we both got ready to leave. We shared a look, and we both knew we were on the same page. We didn’t even hug.

Truthfully, this was the second best outcome I could have hoped for. The best, obviously, was that we both have a great time and agree to do it again. The worst would be one of us thinking this was amazing, the best date ever, while the other planned their exit strategy. That situation led to let downs or being ghosted. The route Eli and I took left us both on the same page, happy to go pursue other things and let this date go.

Pursuing other things was exactly what I decided to do. They couldn’t all be bad, right?


There was the coffee date with the Ivy League student who talked exclusively about the research he was doing—something related to economics and law that I still didn’t have a full grasp on after two hours. He went on and on, barely letting me get a word in unless it was to agree with whatever he was saying. Needless to say, I wasn’t eager to see him again.

Then, there was the dude who worked at the campus radio station. He was from the dog lovers bunch, but unfortunately, he didn't bring his dog to college. The date was a bust, which was a shame because I would occasionally run into him on campus, making for an awkward encounter. On one occasion where we passed each other without saying a word, I was with my friend, Rach. As soon as he was out of earshot, she turned to me and said, “I went on a super awkward date with that guy one time. It’s always weird seeing him and not saying anything.”

I was floored. “I went on a lame date with him too!”

It turned out we had very similar experiences meeting him on CherryPick and having subpar experiences. Neither of us could pinpoint what exactly was wrong, it was just...awkward. I reasoned that if Rach and I both felt it, it had to be something on his part.

With so many guys that were nothing but let downs, I felt even more pressure to hold on to anyone that I felt even a little bit of a connection with. If they could make me laugh and ask me questions, they were a keeper.

I chatted with one guy, Marc, and I felt like we really hit it off. We had an awesome back-and-forth, and I laughed a ton. It felt like everything he said was witty or funny. In turn, I spent tons of time thinking over each of my messages before sending them, making sure to show him I was just as charming as he was. Sure, it wasn’t always easy, but when he called me, and I quote, “the funniest girl I’ve ever talked to,” I knew it was paying off. Too bad all that effort didn’t stop Marc from unmatching me right before our first FaceTime date.

I found myself repeating this gymnastics routine of trying to be exactly what I thought guys wanted when I was talking to them. If he was slow to respond, I would give them his space—even if it meant going days without talking to him. If we had a good time together but it wasn’t clear what he wanted, I wouldn’t push him on it—even though I knew exactly what I was there for. If he made self-deprecating jokes and poor life choices, I simply watched it happen—even if I really wanted to recommend he see a therapist.

In the end, this left me with plenty of casual makeout sessions, compliments over how “chill” I was, and a lack of intimacy from any CherryPick guys. Nothing lasted more than a few dates, and I was exhausted by the end of every failed attempt. These encounters gave me a long list of things I didn’t want, but that didn’t mean I felt any closer to finding what I did want.

Next: When All Else Fails, Create Your Own Bunch

1 · 2 · 3 · 4 · 5 · 6 · 7 · 8