I Tried to Go on 7 Dates in a Weekend

by Jess Schaper 7 months ago in dating

Here's what happened.

I Tried to Go on 7 Dates in a Weekend


Oh gosh. Here we go. So, I've been single for a while, by my standards; I am only 23. I had moved to the city (no, not that one, not that one either) about eight months prior, and I had gone on a few dates but none of them really stuck. Every date I've been on since I've moved here was found on a dating app—I’m the youngest person in my office by 15 years and I only had two or three friends when I moved into my apartment. I've dated (dated (verb) 1. been an official "thing") less than five people in my life and I've slept with at most ten people; I'm decently introverted.


At one point, maybe four months prior, I decided to uninstall all of my dating apps. I had a few piss poor experiences to say the least. One day, out of the blue, I decided, fuck it, I'm ready again. I installed three dating apps: Bumble, Hinge, and Her (spoiler alert: I'm bi). And I went for it. I set up my profile to be the most unapologetic version of myself possible, asserting how much I hate capitalism and how dangerously close to anarchy I am in my bio. Having known how flakey people can be, I decided to send every single person I matched with a message. Every. Single. One. And not just a "Hey, what's up," I'd look at their profile and send them a serious message, and only if they didn't have a bio was I allowed to just say hi with an emoji. Needless to say, lots of matches expired, but a decent amount responded.

It was exciting, but it was also almost robotic. People love attention, and I was paying attention to them. What I realized in this planning process was that I could’ve planned a date five to ten messages into matching with someone.

In all honesty I don’t know how I planned seven dates in a weekend, it just happened.


All names are being replaced for the order they happened in, so I’ll start with “Date #1” or D1 for short. Clearly, I’m not going into all 50+ of the messages that lead nowhere.

One of the first dates planned was also the first date that happened. I messaged D1 because he had something about math in his bio—and I love math (sorry not sorry). The date was planned rather quickly, and maybe within the first six messages we had plans to get pizza Friday night. The exact message he sent me was, “So uh, who broke your heart? Before you answer that, agree to have pizza and drinks with me on Friday.”

At first, a little skeptical, I turned to my roommate and her take on it was, “He cares about your feelings and wants to feed you.” So I went for it. (Also, I told him, Joe, so fuck you, you don’t deserve to be redacted) I felt like D1 and I really hit it off! We were having some fun banter, we found out we both spoke Italian and he sent me memes in Italian. I was excited to say the least.

D2 was actually the last date to be planned. I only remember this because I specifically remember texting him, “My only free time this weekend is before 3 PM on Saturday.” He had a Dungeons and Dragons reference in his bio next to his job title, but the sentence didn’t have an oxford comma. It read like D&D was part of his job, so NATURALLY I had to ask him about dungeons and dragons in the workplace.

D3 is still my friend, and I have to say, D3, you’re WILD. D3’s first message to me was, “Hey, Comrade.” It made my LIFE. The banter was great, and we agreed to meet up for coffee. This was about a week before hand, so we texted a little during the week, exchanged memes, and had some laughs. I was excited to meet him.

D4. Just... I clearly have some bias against D4. I’ll let the date speak for D4 himself, but he was one of the last dates planned, and asked me out to drinks seven messages in (including the messages I sent). I messaged him about books because he listed that he liked to read in his bio.

D5 was another person that I felt I really hit it off with! It started by joking about making vines exclusively for Myspace and turned into creating a fake political party whose mascot was a lizard riding a rhino/bull hybrid, in which the lizard was shouting “1312.” We made tentative plans to hang out on Sunday because he was feeling a little under the weather.

D6 was another one that probably just happened too quickly. I messaged her a reference from her bio and within a few messages we had plans to meet up for coffee in her neighborhood Sunday afternoon. We didn’t talk at all in-between the plan setting and the date.

D7 underestimated me, truly, and I called him out on it. His bio listed that he worked as a “scientist” and I asked him for an experiment I could try out. He said something like “we could work on kinetic energy together.” To which I immediately responded: “That’s not an experiment, there’s no hypothesis. C’mon, I have a high school education.”

Thursday (AKA Accepting My Fate):

I was not expecting this. When I started the week, I did not expect to have seven people I was planning on seeing in one weekend. It was a lot for my tiny, introvert self. I was messaging any friend I knew wouldn’t judge me for it. I needed advice. I needed support. I needed to channel some confidence.

Bless my roommates. When I told them, we planned on me making a PowerPoint presentation that I had to give that Sunday so that we could live out what the bachelor(ette)s would be like in real life. The presentation ended up being wonderful, and gave a deep synopsis of all my dates, including pros and cons of each one. I pulled it out a second time the following weekend when we were throwing a party and some friends I hadn’t seen in some time were asking me about how my life was going.


At this point, I started recording my feelings. I recorded myself getting ready for my date Friday; I literally put my headphones in, hit record when I got out of the shower, and rambled.

I was anxious. I felt like I was going to puke (which was very possible that it would happen, because it has). I ended up taking some of my anxiety medications (as prescribed don’t worry). In the recording, while I was getting ready, I kind of went off about how shitty dating has been over the past few years and got all of it off my chest, into the open. Honestly, relistening to what I was saying to myself was really affirming. I have gotten to this point where I have my best interest in mind, and sort of defined what I was looking for and what I was avoiding.

I was also worried that I was being a shitty person for going on so many dates so quickly without telling any of them. At the same time, I know that I met them on a dating app and there was NO WAY I was the only person these people were talking to on the app, that’s how those apps work. At one point I said to myself, “My life didn’t start when I swiped right on you.” After all the self-talk and getting my face socially acceptable, I got on the bus and I went on my way. (Hell yeah I took public transit.)

I met D1 outside the restaurant and found we’d have to wait over an hour to be seated; this triggered some serious déjà vu to the first Bumble date I had ever went on. This should have been the first red flag, since that date ended pretty badly (with the guy trying to play footsie with me at the bar).

D1 had insisted on this restaurant—I later found out he lived in the apartments above the restaurant—that he loved that place and they had great food. When we walked in, he realized it was Friday night and the place was naturally, packed. He didn’t feel like waiting, we left and walked a few blocks to another restaurant.

The next place seated us immediately, which was great but at the same time, neither of us knew what we were getting into. The place was just super overpriced pasta where they used every synonym imaginable to describe spaghetti with red sauce—no, a tomato sauce infused with basil ISN’T revolutionary and ISN’T worth $30—die mad about it or pay your workers better. We both ended up ordering off of the bar menu and got burgers. They were amazing. We got to talking about video games and really clicked on a bunch of stuff.

Then the death jokes came. I understand joking about death can be a coping mechanism, but it’s possible for coping mechanisms to be unhealthy, and on a first date is definitely unhealthy.

We ended up finishing our food at the restaurant and heading to a bar, where I tried to pay for the first round of drinks and turns out he has the most expensive taste of anyone I’ve ever been on a date with. My drink was like $6, his was $16. And like, sure, maybe if I was 30 and had stable income and a well-paying job, I could throw another $20 down, for his drink plus tip, but I’m 23 and I get paid less than minimum wage before benefits. Regardless, I was having a lot of fun.

He drank a lot quicker than me, and started openly judging me for it—another sign. He was saying he judged people for the kind of things I was ordering, but that he would also judge me if I didn’t order another drink.

Alexa, play "I Saw the Sign" by Ace of Base.

We were at a bar that had a different jazz band every hour or so, so we headed downstairs and stood to wait. We shared a few laughs over the fact that one of the band members was wearing a Dragon Ball Z shirt and we rooted for Goku throughout the whole set. I tried to convince him to open up a mosh pit, and he didn’t. Saddest part of the night honestly.

After a few songs, I was exhausted, so I told him I was going to head home. Drunk and unsure where I was, I whipped out my phone, started recording and pulled up google maps. Cue, my voice, saying “So, I had a lot of fun, but… I’ve dated a lot of men that hate themselves, and I don’t want to date men that hate themselves anymore.” So proud of drunk me, she’s a legend. She went on a four-minute rant about it. She knows her self-worth. Drunk me, however, forgot that the shuttles were replacing my subway line for the weekend so I ended up on a different line with an extra 20 minute walk home.


I don’t know how I pulled off Saturday because I ACTUALLY went on three dates on Saturday.

D2 was a lunch date. This also didn’t have the best of starts because I ended up having to wait like 20 minutes for him to find parking, and we walked into the planned-on café, and straight back out when he realized they didn’t have anything he wanted. Honestly, there isn’t much notable to say about this date--it was short and nothing really out of the ordinary happened.

Except he gave off the wrong vibes for what he was looking for. We had some really deep conversations about the prison industrial complex and the state of homelessness in our community, which isn’t the kind of topics I’d be talking about if I’m trying to hook up with someone. Even in the recording of myself debriefing I thought it was a really nice date. I didn’t even know until a few days later when I’d been getting invites to his bed three days in a row. Sorry buddy, not looking for a hook-up.

D3, as we’ve already established, is a bro. And by bro I mean chill, and by chill I mean he’s actually the Duolingo owl and he’s holding my family hostage (that last sentence fragment will only make sense in our current meme culture). We completely hit it off, we still talk to this day. We made each other laugh a bunch, and he ended up coming over to my party the next week. Not really much more to say about him, another ordinary date with an ordinary dude (it’s a compliment).

D4... Ugh.

D4 and I met up for drinks. I thought this was going to go better than it did, the conversation we had on Bumble seemed okay. He listed on his profile that he was into reading and he was “impressed” by one of my author recommendations. He recommended a bar, and we met up.

Immediately upon walking into the bar I realized that it was not only insanely loud, but I was one of maybe three feminine-identifying people there (out of around 40 people). I told him I was pretty uncomfortable with it, which he ignored. He got me a drink and we sat down. It started okay; I go into every date with a few things in mind to talk about to make the date feel a little more manageable for my anxiety. I blew threw my talking points in a few minutes. At one point he tried to tell me that it wasn’t expensive to live in San Francisco—where he moved from—like ok buddy, sure, if you live somewhere rent free and don’t have to pay for food maybe.

He was giving me nothing to work with, and I mean NOTHING. He made it so hard to talk to him. For example, I wanted to know more about one of the authors we both had read. When I asked about it, he gave a very vague answer. This continued—anytime I tried to start a conversation that would be easy to go in depth about, he’d just give a yes or no answer. I couldn’t tell at first if this was just because it was too loud, he couldn’t really hear what I was asking, or if this was his general personality.

After about an hour, he asks if I wanted to stay there, and I suggested a bar that I knew from experience would be a little less crowded and a little quieter. We took a Lyft to the bar (that we 100 percent could’ve walked to) and it was almost a sigh of relief. He was a little better about talking at the next bar, but we really weren’t connecting—at least I thought we weren’t. About an hour into the next challenging hour of conversation, he suggests going back to his place. Just as many femmes that have come before me, I quickly spewed something from my mouth that was very, very, very, obviously a lie, “I’ve got something I need to do in the morning, I need to start heading home.” Did he ghost me or did I ghost him? Who knows, all I know is I’m very grateful to have not heard from since. I walked out and immediately hopped on the bus home—yes, I did strategically pick a bar on my bus route.


Unfortunately, D5 and I never made official plans. I was fucking exhausted and part of me wanted to cancel on D6 because of that. I didn’t have the emotional energy for it at all, so D5 if you’re out there, I’m sorry, I still doubt if I could go back in time I’d do anything different.

D6 and I had an alright date. We had okay things to talk about, but it was just one of those dates where we didn’t really click. We didn’t talk much before planning the date either. The date itself was meeting up at a coffee shop and going for a walk. There was nothing really noteworthy about the date. And I think that’s what made me eventually just let her down easy.

D7 ghosted me during the date planning phase. I think it’s kind of funny actually.

Roommate Reactions:

So I actually went through with the PowerPoint idea, and did a whole presentation for my roommates. They were so vocal about each person and they were both super supportive. I did make it very much like my personality, and I added graphs and charts to be a little ridiculous. We laughed, we had fun, but ultimately, we all came to the same conclusions. Bless you both.

My Own Personal Debrief:

Re-listening to my recordings of my thoughts has been really helpful and affirming. I feel like a lot of the time, I can normalize a lot of shitty situations, so having so many dates in a row was like a good reset for my expectations, really think about my values and what I want. Dick is abundant and low value, don’t settle for less. At one point in my own personal debriefing recordings, I said “If it wasn’t for the amount of dates I went on this weekend, I would’ve settled for less… I think he would’ve been really good for four years ago me, but I’m not four years ago me, I’m today me… It took so much for me to be independently happy, and I don’t want another person to rely on me to be happy.”

Over all, I learned that living in a city is way easier in terms of meeting people that fit your niche interests. I am deserving. While I can plan a date five to ten messages into talking to someone, most of those dates are GOING to be lackluster. I will find what I’m looking for, and I shouldn’t settle for less.

Jess Schaper
Jess Schaper
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Jess Schaper

I'm just as unimpressed with you as you are with me. I have too many interests. 

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