A wild two months on the dating apps

Reflections on modern dating

It sounds weird that I’m 33 and have barely dated but it’s true. I’ve fallen into relationships but never had that phase of my life (until now) where I was Dating, official verb, going out to casually meet different people with the intent of evaluating them, and picking someone to be in a relationship with.

Until a couple months ago, the extent of my online dating experience was:

• Downloaded OK Cupid once in 2018, hated the UI so much I deleted it again before talking with a single person

• Downloaded Hinge in 2021, made it to a video call with one person. Realized I was too busy to date and cancelled any plans I had started making with anyone. One guy wound up being super creepy about it and finding me on other channels off of Hinge and I felt like “That’s enough of THAT” and was not tempted to try again until…

Now.

I’m not sure what exactly made me want to try it. I’m pretty happy single. But on the other hand, there wasn’t anyone in my existing social circles I was tempted to date and online dating seemed like a way to meet people I wouldn’t otherwise. Whatever the reason, decided I wanted to give it a shot.

My criteria

Chemistry is a mystery. So not to disappoint any bitter readers who want to complain about women all swiping on the same 5% of men who are 6 ft tall doctors, here’s where I landed on my filters:

• no moderates, conservatives, or apolitical people

• no one who wants kids

• no one super religious

• someone I can have fun with even if we are doing nothing

No kidding. Not a size queen, height queen, not screening on careers or income or race. I do have a couple of physical preferences which, given how broad I’ve been otherwise I let myself keep:

• I prefer not to date super slender men

• Not a huge fan of redheads

• Not a huge fan of gaged ears, although otherwise don’t care about tattoos or piercings

• Not a huge fan of men with long hair past shoulder-length

I had some other miscellaneous preferences that are the OPPOSITE of what people would probably expect.

• Prefer NOT to date doctors or lawyers

• Prefer NOT to date other tech people

• Love some scruff or short beard

• Automatic no if the dating profile pic is of a fish or someone with a shirt off

• Prefer people 5+ years older than me but not so old we have no shared cultural references. ~7 years older seems to be a sweet spot for that

Berserker mode

Going in, I downloaded Hinge only in late September. (Since then, have added 2 other apps). As I was putting together a profile a mix of complaints about online dating floated around my subconscious. The shallowness of swiping, people with misleading profiles, guys who send passive-aggressive Venmo requests for meals they paid for after a woman rejects them.

I originally set out to avoid these pitfalls with the following strategy:

• Swiping DID feel shallow, so I decided to try to do coffee or video chats with anyone that seemed aligned to what I wanted

• I was committed to paying for my own food/drinks/whatever. Number one, I have money. Number two, for the amount of social equality I want from a relationship I’d expect equality on other matters. Number three, I figured I could avoid the snarky Venmo requests after rejecting people

• Obviously, I couldn’t control if other people had misleading profiles, but for mine, I deliberately chose pictures of myself that weren’t my favorite. I wanted people to show up and think I was better looking than my pictures

This plan wasn’t terrible, tbh?

Rusty as I was dating I expected awful nerves, but quickly with my “meet everyone once” strategy I would be booked with five first dates a week. The sheer volume made it too commonplace to make me nervous.

I had at least a month of dating at the pace of 4-5 dates a week, and at first, I felt great about my plan. The hectic level of scheduling meant that I didn’t wrack my brain trying to think of creative dates, and people would just catch me with whatever I would have already been doing that day. Maybe it would be a hike, maybe I’d be at a favorite brunch spot, but they’d get a more real glimpse into my daily life.

Because of my absolute blitzkrieg of dates, I don’t know how many individual people I’ve dated in these two months. Maybe 10+? Primarily first dates that didn’t go anywhere.

At first, it seemed hilariously fun that in a random week I might kiss one boy Tuesday and another Wednesday, like ??? When was the last time that was true in my life? People showed me hipster spots in Durham I never knew about. The exploration and possibility were really fun initially.

As a 33-year-old woman, I was also interested to find that the incel talking points about how undesirable women of my age are seemed laughably wrong. (I am yet to have be rejected by anyone, although when it does inevitably happen there’s nothing wrong with it and I’ll be fine).

Although not the worst plan ever, it was unsustainable. Five dates a week was…tiring. This leads me to the next section, where I talk about the experiences from dating that were most tiring and made me end berserker mode dating.

Review of men on the apps (more normal gripes)

The main thing that makes me reject people both before and after meeting them has been: they are boring.

Before we meet, this looks like all the profile cliches rolled into one: “partner in crime”, your Myers Briggs type (yuck), Harry Potter (can we just move on please), “looking for my person”, “drama free”, “chill and laid back”, or one sentence bio “message me to learn more about me”.

After meeting people, this looked like not being able to hold a conversation or banter, not being very funny, not being able to “yes and —” the conversation to somewhere more interesting than the basic first date topics.

With my extremely broad approach, I also went on a lot of first dates where maybe the person wasn’t my normal physical type but I thought they seemed cool and wanted to see if chemistry developed. In the past, I’ve dated way outside my type for at least half of my relationships so I’m not overly rigid on any specific physical criteria. But in many of these cases, physical attraction did not develop and I felt as if I may have wasted their time. With too many dates to schedule already, this has segued into a phase of me adding more criteria for who I agreed to meet.

(It is kind of damned-if-you-do, damned-if-you-dont on that, I’ve realized. The same guys haranging me for wasting their time are also no doubt the ones whining about how no one gives them a chance. I’ve realized there’s no winning that one).

Less normal gripes

Have DEFINITELY had a few moments that made me go, “are people OK?” during this round of dating.

Multiple men have repeatedly told me I make them nervous. Some of them have seemed to feel embarrassed about their financial status or career or both. Some have seemed to oddly put me on a pedestal. More than one has made running comments about how I would inevitably dump them at some point.

I feel like I’m being “girlfriend-zoned” very early into dating. Instead of fending off advances from overly forward guys or trying to suss out players and f@#$bois, people are being almost confusingly chaste and proper, like they don’t want to offend me.

As a random white lady, I also did not foresee that I would have multiple race-related faux pas disrupt dates — coming from the OTHER party.

One guy I started dating of Asian descent (trying to keep some anonymity for these guys so not going to be more specific) went ON. AND ON. AND ON about how beautiful he finds Jewish women after learning that’s part of my family background. He sort of looked me up and down after hearing I was part Jewish when I did my and went, “Ohhhhhh I see it” then launched into this rant about the beauty of Jewish women. I felt (then and now) so WEIRD about it, ahahaha.

Another biracial man dropped randomly at the end of a second date that he only dates white women. That was the first date event that had my jaw on the floor. Many stereotypes normally lead to people feeling that way and spoiler, they are not flattering to anyone involved! Did he imagine just because I’m in the group he deigns to date I’d be flattered? Swing and a miss.

Most unusual gripes

I have had two total “What. The. Fuck” moments during this round of dating.

The first was when a guy I had great chemistry with up until this point had me to his house for the first time. In the middle of our cute sexy date he announced that because his house (which was very pretty and in a great area) had only one bathroom, he normally would go out back and pee in the woods(!)

As I was leaving this date, I momentarily forgot my phone and went back to get it and there was this guy, PEEING BEHIND HIS HOUSE. I averted my eyes and yelled “forgot my phone!” sprinting into his house and dutifully not looking as a hysterical bubble of laughter threatened to escape my lips.

Maybe this guy is an eco-warrior. Maybe I shouldn’t be so judgmental. But I learned about myself, I am not ready for that information or to see you peeing behind your house on the ~3rd date.

The second happened more recently. A normal good first date for me is to go to Boxcar, a barcade near me. Because there are activities some of the pressure to establish a rapport with a stranger is lessened. If things go well, there’s a fire outside where you can just talk and get slightly cuddly. If things are strained, you can focus on the games and it usually doesn’t manage to be too bad of a night even if the date is a bust.

WELL.

The guy I saw on this date asked me my favorite game, and after we played was so ruthlessly rude to me about not being better at it that I wound up calling him rude to his face.

I’m unclear if this was an attempt at negging, which hadn’t happened to me up until this point. If it was, it went quite poorly for him. I called him rude to his face point blank, and then said something along the lines of, “I mean, I was a cheerleader in high school I was at parties not hanging around an arcade all day. And if you’re looking for someone to be super serious and competitive about these games you’re going to be disappointed because I literally don’t care and am just here to have fun”. That somewhat shut him up.

I find the motivations of this person fascinating. If you want to be terribly superficial I was probably out of his league looks-wise, so was it nerves? Feeling like being good at games would impress me? I can’t speak for every 33-year-old woman out there but I assure you it did not. A joyless bad sport who thinks it is impressive that he’s clocked five million hours on Guitar Hero, I’ll try not to swoon.

I’m also not even bad at games. I normally beat most people that I’m with at at least some of the games, nerd upbringing or not. This guy was really next-level. At one point he sort of complained about me beating him at Mario Kart because he’s “so good at it” and I took the lead late. I literally cannot think of a less attractive behavior in a ~40 year old dude, like what even.

Being meta for a sec

It didn’t really take that long for me to go from “Oh online dating isn’t as bad as they say” to “Ahhhh ok I get it”.

I see how online dating keeps people feeding into the system, for one. After dating so many people and not feeling any real connection, so far rejecting each and every one of them: I felt far lonelier than I ever did just being single. It is like being in a crowded room and knowing not a single person in it would understand you. But because I feel lonelier, I feel more motivated to try to alleviate the loneliness so what do I do, log back onto the apps.

I now understand the dysfunction of the shallow swipe culture we all love to hate. The arbitrary, superficial criteria people end up using are just a proxy to make the amount of conversations manageable. It is like how jobs that don’t need a Bachelor’s Degree sometimes require it, just to filter some chunk of candidates out and make the search less vast. Although my whole “first date for everyone” approach was interesting, it was exhausting. I understand why most people can’t do that.

At this point I also feel like I have a new awareness of the implications of how men and women approach the apps. I think I knew already from listening to Why Won’t You Date Me that many men swipe on everyone and then wait for responses to actually consider if they want to talk with you.

But I have realized there is an extension of that logic that says, maybe the reason I have to keep rejecting everyone is that men will just continue to see where the dating goes if they find you remotely physically attractive just in case sex may ever be on the table. Some of the people I’ve talked to, I have felt that we had so little rapport that I am SHOCKED to hear they want to go out again. Is it just the logical accompaniment to the swipe-on-everything mentality? Maybe. Maybe they also felt we had zero rapport but thought, “let’s roll the dice in case I get lucky”.

The net effect of my point above is that while I have plenty of choice and dates every night I have energy to go on them: I really have little to no idea if anyone actually meaningfully likes me, or if they just find me attractive. It’s slightly disorienting.

Bottom line on that is, although I used to more agree with the idea that the apps may be somewhat harder for men than women, I am no longer so sure.

What next?

Well, I’m giving up - sort of. I’ve backed off online dating and focused more on in-person hobby groups for the time being. If my feelings change in the future, maybe I’ll start again.

Even though it has been such a highly mixed bag, I do feel that the weird stories have made up for some of the horror.

Thanks for reading and catch you next time.