Two big things happened when I turned 18: I registered to vote, and I downloaded Tinder. I lived at home in a suburb of 8,000 people north of New York City. I was still in the closet. While my hometown is more liberal than most, I didn’t know many gay people in the area. Sure, I had heard about other gay men who were friends of friends, but given I had never actually met them, it wasn’t like I could hit them up and ask them to hang out. So, I took to Tinder to meet them and to try to discover what I was looking for — either in a romantic partner or new friends. Perhaps first and foremost, I did not want to go to college without ever having kissed a boy.

So I went on a lot of first dates. Twenty in less than two years to be exact. I took notes — literally. Using the Notes app, I kept a detailed record inclusive of every person I have been on a Tinder date with — their name, what school they went to, and where we went on our date. I figured that at some point in my life I might want to reflect on those experiences, and here I am.

Date #1

Jack* had just finished his sophomore year of college while I had recently graduated from high school. We met in New York City, walked around Central Park, and sat in the grass. We talked for a while and had a good time, but it quickly became apparent that he was bad at texting, horrific at making plans, and generally unavailable. While this was my first date, he had been in multiple serious relationships. There was an overall dynamic that just could not work. It was clear I needed more time and experience to understand what to expect from another guy.

Date #2

Grant and I walked around Manhattan’s Madison Square Park. (Do you see a pattern with what I like to do on a first date?) It was fine, but he talked about his ex almost the entire time, and I should not have to explain why that’s a first-date faux pas.

Date #3

Brett* and I were going to colleges in the same area in the fall. I invited him out with my friends, and he was really rude to them. When one mentioned the guy she was currently seeing, he flat-out called that guy ugly. If this is how he was going to act when trying to make a good impression, I could only imagine him at his worst. If your friends and your date do not hit it off at all at the first meeting, consider carefully whether or not this person is worth possibly damaging your friendships.

Date #4

Tom* and I met at the Museum of Modern Art and then walked around Central Park. Talking about our art preferences easily evolved into speaking about our preferences in other areas. We dated for a few months after that, caught in this weird limbo where neither of us had put labels on anything. I knew he was probably seeing other people, but I clung to hope that we were exclusive. Nonetheless, I never voiced how I felt, which led to the dragging out of much nonsense. Don’t be afraid to ask someone where you see something going, whether or not you are ready for the DTR talk.

Date #5

I went out with Leo* when I arrived in Washington, D.C. for my freshman year of college at George Washington University. Leo and I had been talking on Tinder for about two weeks, but neither of us were making moves to meet up. I ended up taking the initiative and asked him out. We ate some Mexican food, watched a movie together, and it was a relatively fine first date. But he had just gotten out of a relationship, and he admitted he was not ready to start dating. Sometimes whether things work out is out of your control. Blame timing.

Date #6

Benjamin* and I went to see “La La Land” while I was home in New York for break, and the entire date had this weird, palpable tension — we never even really made eye contact. I had low expectations, given the distance issue looming, and I probably set myself up to fail. We shared an awkward hug goodbye, and I never heard from him again — nor did I reach out to him. But the reality is, he went to a school hundreds of miles away from mine, so I doubt things could have progressed. Meeting someone over break can be fun, but if you’re looking for something serious, you risk setting yourself up for disappointment.

Date #7

Mason* was a little bit older than I was — he had just graduated college. I didn’t expect that this would be a deal breaker, but I wanted something casual whereas he wanted to immediately settle down. I learned that while age may not matter, where you are in life definitely can.

Date #8

I was home for summer break, and the fact that I was leaving in three months meant I wasn’t looking for something serious. I neither admitted that to myself nor to Jack, and I fear I led him on. It’s hardly necessary to go in with the mindset that you’ll meet your husband, but knowing whether or not you’re merely searching for friends is a good idea.

Date #9

My date with Daniel* was not what I anticipated. It was my first date after transferring from a school in Washington, D.C. to a one in Boston, and my goal was to meet a guy who would make me happy and be my rock as I navigated the change. Though the romantic vibe wasn’t there, Daniel is now my best friend at Northeastern. He has introduced me to a lot of his friends, who I’ve also become close with. This was the most surprising — and definitely most formative — experience I’ve had from a Tinder date. I figured out that Tinder is not just a means to find a knight in shining armor to pick you up from your castle; it can also be a catalyst for meaningful, non-romantic relationships.

Date #10

Kris* and I matched over the summer, and we talked for a while before we met in person — too long, in fact. Our relationship was already closer to a friendship, and trying to take it in a different direction felt plain weird. Stop stalling, people.

Date #11

Oh, Brock*. This was my second time going on a date with someone from a prestigious college, and he lived up to all of the worst stereotypes. He spent the entire date trying to impress me with how smart, busy, and well-traveled he was. Someone who spends an entire date trying to convince you how perfect they are is probably overcompensating for something. Unsurprisingly, there was no second date.

Date #12

Clark* is one of the few guys I went out with who also went to my school and was in my year. We met for coffee before my 9:35 a.m. class, because that was the only time we were both free. The date was OK, but we spent most of the time talking about how stressed we were applying for summer internships. It got to the point that it began to feel like a competition. The fact that we were duking it out rather than trying to genuinely get to know each other was a red flag.

Date #13

Jeff* and I walked around his neighborhood before deciding to go back to his house and bake cinnamon rolls (can you say goals?). This was an extremely fun first date, in no small part because it ended with a delicious snack. While Jeff was kind and I had no complaints, we weren’t right for each other. Nonetheless, I highly recommend baking on any and all dates.

Date #14

Edgar* was a musical theater major at a neighboring college. I am a lover of musical theater despite my horrific voice. We got coffee, talked about his major, and laughed a lot. It was fine, but I left feeling like there wasn’t a spark. Just because nothing bad happened doesn’t mean two people should continue to pursue each other.

Date #15

Paul* was a recent graduate of a nearby college. He was an interesting character and quite eclectic, but he got in more words than I did. A lot more. Anyone who knows me knows I am not quiet, but anytime I tried to talk, he would start speaking over me. I felt like I was listening to his podcast. He could’ve been nervous, but failing to give your date a chance to speak is a deal breaker.

Date #16

Oliver* and I met while I was studying abroad in London. We bar-hopped to his favorite spots, and he paid for all of my drinks, because he was an investment banker and I was (and still am) a poor college student. Nothing came of the night, but it was fun to experience London through the eyes of a local. I’ve continued to use Tinder while traveling, because I’ve found the people I meet can provide authentic (read: non-touristy) experiences.

Date #17

My first date after returning to Boston from London was with Hunter*. I was busy settling back in, and, once again, I didn’t stop to think what I wanted out of a date. When that happens, I find I am not fully there for the experience. No one wants to hear that their date is there for some unknown reason, so get yourself sorted, at least a little, beforehand.

Date #18

I went out with Emmanuel* because we shared an interest in in urban studies. We were both political science majors with urban studies minors; it seemed perfect. But when you base a connection around a singular thing, it leaves a lot to be desired. We talked about our ideas and thoughts on public transportation, but I felt more like I was being graded than getting to know him. Similar passions are great, but forming an entire romantic relationship around them is unlikely. You need to be able to have a diverse range of conversations.

Date #19

Henry* and I had been talking on and off for about a month. It was one of those things where we figured we might as well meet up, but it quickly became evident that there was no real connection. He loved Mariah Carey; I loved Ariana Grande. He had conservative views; I have liberal views. We could not agree on anything. Opposites may attract, and I’m all about getting out of my comfort zone, but having some common ground is non-negotiable.

Date #20

Drumroll, please: This date was with my current boyfriend. We went to my favorite museum in Boston and then sat outside for hours talking. In the bitter New England cold, might I add. The conversation was so natural and easy that I texted a friend after saying it was the best date I had ever been on. We both made jokes about the art, and discovered we have the same dumb sense of humor, musical tastes, and love of video games. There hasn’t been a dull day since.

*Names have been changed to protect innocent daters everywhere.