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

    I just wanted to live my best rom-com life.

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

    selfie of the author

    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.

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

    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.

    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!

    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.

    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!

    author taking a mirror selfie

    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.

    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.

    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!

    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!!

    author taking a selfie on the street

    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.

    author selfie in the street

    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.

    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.

    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.

    author rolling her eyes

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

    cartoon characters with text, then everything changed when i got to date 6

    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!

    author listing to taylor swift "fearless" after the date

    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.

    author selfie on the street

    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!

    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.

    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.

    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!