I Decided To Go On 7 Dates In 7 Days And I Honestly Learned So Much

Hi, I’m Hannah, and much to the chagrin of my parents and puzzlement of my friends, I don't really date.

I rarely date for a number of reasons. Number one is that it has never been a big priority for me. I’ve never felt quite the same drive to date or enter a relationship that my friends did.

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While I do still feel attraction to people and have interest in pursuing a relationship, both have definitely felt lower than the average person’s (though this is my perception, and there is certainly no “normal” level of attraction or dating interest to feel!).

Number two is that meeting new people in general, and ESPECIALLY in a dating context, fills me with an overwhelming sense of dread.

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My social anxiety, combined with the fact that most of my past experiences have been negative, really just creates the perfect anti-dating cocktail.

I do occasionally dive into the apps to see what's out there, but I quickly get overwhelmed, and then delete them for another few months.

And number three? Frankly, I just don't usually feel like putting the effort in! Finding a partner is important to me, but in a vague "one day" sort of way. I've pushed it off for a long time, telling myself that I'll be able to tackle dating later once I've gotten the rest of my life in line.

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But I'm starting to realize...my life is never going to be "in line," lol. And if this is important to me, I should give it an actual shot!

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Besides, my anxiety's a lot more manageable than it used to be. I've tackled lots of other scary things, so why not this?

I decided to dive right in and make up for lost time...so I planned 7 dates in 7 days!* I used dating apps (Hinge and Bumble) for convenience's sake, and also because having to find people to ask out in person would've made this take way too long and be ever farther out of my comfort zone. For every date, I decided to meet for a drink** so that they’d all have an even playing field and be conversation-focused.

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*My reasoning: I know from experience that dipping my toes in doesn’t work for me. I’ll pat myself on the back for a small effort and use it as an excuse not to do anything else for months. So I decided to throw myself into dating — also because the more often I do something, the easier it is. I figured if I could make dating feel routine, it wouldn’t be quite so scary. Plus, I wanted to be so busy I could hardly even think about what I was doing.

**I came to regret this after drinking seven nights in a row, lol. More on this later.

Alright! Now, with all that out of the way, let's dive in!

Note: I’m not going to use names, photos, text screenshots, etc for privacy, and also because I’m not doing this to judge anyone else’s dating “skills,” or lack thereof, or personalities. So if you were expecting a juicy exposure on seven different people...I am sorry.

DATE 1: Right off the bat, I was suuuuuper nervous. Like, about-to-puke nervous. I went pretty casual with my outfit, and I'm not sure the all-black helped me look very approachable*, but oh well. Here's what I wore!

It didn't help that my date was late, so I just sat there with anxiety building for a long time. But once the date started, I immediately felt a lot better. We actually had a lot of things in common, and I felt we really matched each other intellectually. Right away, this made me feel better about dating. It kind of just felt like grabbing coffee with an acquaintance or like, a cousin you don't know that well.

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We talked through a wide breadth of topics ranging from politics to how much you can divorce art from the artist to the best and worst Pixar movies. The conversation was extremely natural and there were no awkward silences.

Before you make a joke about dating cousins, I think this feeling probably should've been my first clue that...I wasn't really feeling it. Which really sucked, because the date otherwise went well. But the chemistry, or the attraction, or the ~vibe~ just...wasn't there.

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I've tried to continue to date people where it's just not there before, in the hopes it'll come later, and it never has, in my experience. It just leaves me feeling resentful, frustrated, and guilty.

I remembered another reason I hate dating after this date: and that's the guilt. Like I mentioned, I don't feel attraction/chemistry often, and I always feel so guilty for wasting people’s time. I feel like I’m blindsiding them when I reject them after a date that technically went very well. I almost feel like if I knew there was nothing there, I should’ve cut the date off after 20 minutes and not “led them on” by continuing to speak and being interested in the conversation. My philosophy is that if we’re already there and having a good time, why don’t we just continue talking even if I know I’m not romantically interested?

This fear feels very rooted in messaging to women about what they “owe” men, so it’s probably not super valid, but I feel it anyways.

DATE #2: I completely forgot to take photos for this date, except for my BeReal, of course. So here's my cat and me for your viewing pleasure. On to the date!! I was really shocked about this, but right away...y'all, I was feeling it.

But...a second thing that sucks about dating that I'd sort of forgotten while I was planning this was that sometimes, even if you're feeling it, the other person might not be. I didn’t hear back from this person after our date, and that’s completely fine, though obviously, it sucks!

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It’s still a good experience, and I felt proud of myself because I felt like I was really myself. Maybe slightly rambling and awkward at times, but still myself. Maybe I could’ve put my best foot forward a little better, but I think that's mostly my brain doing the classic, "What'd I do wrong???" thing when really, there could be any number of reasons it didn't work it.

DATE #3: Sorry for the blurry photo...anyways, I went into date #3 with newfound confidence, mostly because of #2 (I didn't know I'd been rejected yet, lol). Dating wasn't so bad! At best, it could be exciting and fun, and at worst, it could be a chance to have some interesting conversations!!

DATE #4: The high had sort of faded by the time I got to the next date, though. I was tired of dating and tired of the bad nights of sleep I was getting from drinking, and my stomach wasn't liking all the anxiety I was putting it through. But still — I had no reason to believe, based on my first three dates, that this date would be bad, so I slapped on some makeup — though the same can't be said for a smile — and headed alllll the way to Brooklyn.

Aaaand...my experiment came crashing down. Y'all...this date was bad. Like, so bad I wrote down every awful thing he said in my notes app afterward so I wouldn't forget, and I still think I forgot some. This is the only date I will be a little more specific about because this guy was a racist misogynist. I'll get into some of the stuff he said below, but the main thing was that HE GUESSED MY BRA SIZE after steering the conversation towards boob jobs. I mean, he was right...but that was almost weirder.

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He was very combative and would accuse me of "getting mad" at things he was saying when I was sitting there completely calm and polite, and he was the one getting worked up. He went to an Ivy League school and said he didn't like it because it was full of nerds. When I said I was a nerd, he said he does like some nerds because he "has lots of Asian friends." He weirdly bragged about his parents loving him when other people's parents don't, used ableist slurs, talked about "outsourcing dating app conversations to India," asked me what I think of trans people in sports, and said he doesn't think they should be allowed, and told me his only interest was "going to bars" (I was actually really surprised at how many of my dates listed drinking as their main interest or who couldn't think of any interests, and I learned it's really important for me to be with someone who's passionate about something). At one point he asked me how the date was going on a scale of one to 10, and I refused to answer because I didn't want him to get angry.

I know I should've left earlier, but we hadn't paid yet or finished our drinks and I felt really uncomfortable and unsure how to end the date without him getting angry at being rejected. I really had no idea how he might react, considering I didn't know him at all and he already seemed to be getting worked up at my...facial expressions as he was talking, I guess? I was also very far from my own neighborhood and didn't know that neighborhood well, whereas he lived down the block.

I'm telling you all this not just to shame him, but because I really want people to know that this experience, based on some of my past dates before this experiment and from talking to friends, is not rare. It's one of the shittiest parts of dating strangers (and if you're thinking well, maybe she shouldn't have gone out with a stranger, you're part of the problem).

This reallyyyy had me questioning if I even wanted to continue. It made me think of a few problematic things some of my first few dates had said, as well. And I started to wonder if I was being too picky in not wanting to be with someone who says problematic stuff.

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After the week was up, I thought back and almost every date said something problematic. I'm not the cancel police or anything, but it really sucks when you're two hours into a date and they say something intensely fat-phobic out of the blue, or casually tell a "funny" story about their friend that sounds suspiciously like they were sexually assaulted (which suggests they don't understand what's included under sexual assault). I'm sure I've said problematic things in the past, too, but I just don't think I'm willing to be with someone who isn't, at the very least, actively doing the work to try to un-learn inherent biases and problematic views. After some thought, I decided this wasn't asking too much, and that I'd much rather be alone than with someone where I constantly have to be apologizing for them and challenging their long-held, potentially really toxic beliefs.

Still, it showed just how common and normalized these kinds of beliefs are and made me challenge my own pre-conceived notion that most people I meet (who call themselves liberal) are not fat-phobic, racist, anti-gay, anti-trans, or misogynistic; and that they understand things like consent and support abortion rights. Since I know that's a non-negotiable for me, I learned I'm probably going to need to be really upfront about these things and probably put them in my dating profile, even if that feels awkward. I also know I need to do a better job at challenging these comments rather than just going "oh, that was a fucked up thing to say" in my mind.

DATE #5: I was not feeling too great at this point, readers. I was in a MOOD, and I really, REALLY just wanted to watch Only Murders and eat ice cream with my roommate. Ultimately, I persevered, but as you can see...I was not excited.

I'm sorry if this is depressing so far. Trust me, I get it. But...EVERYTHING CHANGED.

DATE #6: Please ignore my hair and makeup in this picture. It was taken post-date after we had to run through sprinklers. IT WAS THE ROM-COM MOMENT I HAD BEEN WAITING FOR.

I practically skipped home to tell my roommate all about it, and she was teasing me since I'm NEVER bubbly. I realized something very obvious after this date, that I think most people know but I never really believed — dating can be fun! Like, the date itself — it's not just a means to find a partner you might one day have fun with! Still, I was hoping this would turn into something. I definitely wanted to see him again!

DATE #7: Unfortunately, I had one last date to get through. And that's kind of how it ended up going...like something to get through.

Finally, FINALLY, I was done. I was exhausted and relieved, but mostly excited. My experiment had actually worked! I found someone I was excited about! LOVE WAS REAL AND IT WAS IN REACH!

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And then it all came crashing down for the second time in a week, because I discovered date #6 was only in the country for a few more weeks before moving.

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I know we only had one date, but I was still pretty sad. I've had a lot of "almost" flings that had potential that ended due to circumstance (or never really began), and so this happening again made me go, "Welp, maybe I'm meant to die alone after all." But that's me being overdramatic. If you couldn't tell from the above gif, sometimes I do that.

STILL. While I didn't actually end up finding someone to date, I think my experiment was a success. I learned you have to kiss a lot of frogs, so to speak, but that it's not impossible for me to find someone I connect with. It just takes a TON of work.

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Between swiping and messaging and getting ready and travel time and then actually going on the dates, I basically had no time to do anything else for a week — and for a couple of days leading up to it — but work. It was a lot of work for very little return, and as someone who doesn't feel chemistry often, it's frustrating to realize just how much work I could put in for hours and days and weeks and years and still not find someone.

But this also made me challenge my idea that I don't feel chemistry much. I felt it twice out of seven times! Even though those people were pre-selected as people I thought I might have chemistry with, it was still positive for me to see that it's not as rare as I'd thought.

Most of all, this helped SO much with my anxiety over dating. I actually recommend this process if you really struggle with anxiety over dating. It helped me see that it's not as scary as I thought! I would definitely not recommend grabbing a drink for every date, though. Coffee would be better, though if you work during the week like me that's tough — maybe just a walk, if it's summer?

Here are my final takeaways!

—I definitely am going to put something about my beliefs in my bio. I was scared to come off too strong, but it's just a waste of time to meet people who aren't meeting the bare minimum of being a good, conscientious person. I feel like my profile before was more of like, an "advertisement" for myself, and I was so focused on being wanted I forgot what I wanted. I also think I can be more upfront about wanting a relationship, not a fling before someone leaves the country. (I do have "relationship" in the "looking for" section, but maybe I can be more vocal about that in talking on the apps). Again, I was scared to come off too strong, but that's only going to lead me into situations where both parties end up disappointed because we don't want the same thing.

—I think I can stand to be a lot pickier. I swipe on a lot of people whom I think I might potentially be attracted to, but it's kind of a wild card where I can't really tell until we meet. I also give people the benefit of the doubt if their profile is kind of boring. But the two dates I felt the most chemistry with were the same two that I felt most attracted to on the apps (though there have definitely been times in the past I felt very attracted to someone on the apps and didn't feel it in person!). They also had strong profiles that showcased their personalities. I think I have this really toxic internalized belief of, like, "every guy deserves for you to give him a chance!" when, really, there's nothing wrong with being picky — after all, I plan to be monogamous and find a life partner, meaning there's only one person in the entire universe I can choose. While I may miss out on some potential partners, being super picky will provide a better chance of having a good date, and will make my number of matches more manageable.

—Overall, I seem to have a lot of internalized beliefs about dating that are worth challenging. Especially in regards to rejecting people and the intense guilt I feel associated with it; I need to remind myself that I don't owe anyone anything. I talked about expecting the people I date to at least be working on challenging their own long-held beliefs and biases, and I need to do the same to my internalized misogyny. I really thought this was something I'd already tackled, but it's become clear through this process that there's a lot of work still left to do!

—And finally, now that I've tackled this, I definitely want to try to tackle meeting people organically, without the apps. There's nothing wrong with the apps, but as I said, it's hard for me to tell how I feel without meeting someone in person, leading to a lot of time wasted. I want to get better at being approachable and approaching people in the future. *Sigh* That's the worst part about tackling something you are scared of — it feels like there's always something harder to tackle once you get it out of the way.

What's been your experience dating as someone who didn't date much in their teens and early twenties? Let me know in the comments below!