30 Days of Online Dating: What I Learned

This is a modern dating experiment. One girl. Five dating sites. Hundreds of chats. Thirty days. Thirty dates. Eighteen guys. One boyfriend. To start at the beginning, click here -- or jump right in at the conclusion below.


If you're reading this, you're most likely aware that I once decided to go on 30 online dates in 30 days and (over)share my experiences with complete and total strangers. (And yes, you too, Mom.) The actual 30-day period took place in the fall of 2013. Why did it take me a full year to begin writing about it? Let's just say it was a rough and bumpy road to recovery.

This brings me to the warning I should have placed at the beginning of this experiment. If you cherish your soul, do not try this in your own small-but-full-of-character studio apartment. Am I glad I did it? Absolutely. Are there things I'd do differently? Probably not, because I don't believe in learning from my mistakes. Are there things I should have done differently? Indubitably, but I try to avoid admitting when I'm wrong, so we'll go with... nope again. (Yes, I can play this game all day.)

Here is a brief, self-asked/answered Q&A to wrap this sucker up:

So wait, what happened with Tinder Oliver*?!

Remember that Tame Impala concert we were supposed to go to? We never made it because we ended up attempting to grab a "quick bite" before at Alma. That quick bite turned into an intimate** three-hour dinner followed by a scary movie back at TO's place. Where there was a toothbrush. For me. Like, my own toothbrush. This was a big step up from the last time I had a toothbrush at a guy's place (purchased/placed there by me) and he later texted me, asking if I could come pick it up/remove it. In short, I took this super-romantic dental implement as a sign that we were exclusive. (I think I was actually right this time.)

Fast-forward four days to us at another dinner. TO tells me his parents are "quite curious" about me and then jumps into a big reveal about a super personal family situation. I decide that this is probably the appropriate time to come clean/tell him he was part of an experiment. Words cannot describe the awkwardness of this conversation. (Well, there are probably a few that could, but I'm pretty sure they're medieval/or German.) I decide to start by telling him that my mom calls him "Tinder Oliver," Tinder included. When he shifts somewhat uncomfortably at that, I know we're in for a more-than-slightly torturous tete-a-tete.

All things said (too many things, some might say) and done, he pretended to be OK with it, but I'm pretty sure he never was. Actually, I know he never was because in the midst of our nothing-if-not-memorable break-up, he used the phrase, "that's not normal" in reference to this project. That came seconds after he told me his attraction to me had most likely been Oedipal in nature, so the brusque dismissal of a fairly transformative experience barely bruised my newly battered (and utterly grossed-out) sense of self.

This answers my next few questions:

1. Are you still together? No. The first two months were magical/wonderful/easy/full of I love you's (him), meeting parents (us), and pick-ups from the local jail (me)(more on that [much] later in another, still-to-be-written post). At week eight, the relationship did a complete 180 and became confusing/weird/emotionally destructive. I apparently "ignored a lot of red flags" (another quote-pull from aforementioned break-up), and to be honest, when sh*t went south, I spent most of my time trying to figure out what I did wrong/who he wanted me to be, which wasn't great for me, my sanity, or our relationship. (Or my writing, for that matter. Turns out, not everyone pens their best sh*t at their darkest hours. There goes that heroin habit idea.)

To sum it all up, we covered a lot of emotional ground very early on/internally combusted a few days before Christmas. Unfortunately, the super cute inside joke gifts I had purchased for him were non-refundable. Fortunately, the orchid I had purchased for his mother, as I was supposed to be attending their family holiday celebrations, was also non-refundable. That indulgently pricy blossom was a true f*cking beauty/looked amazing on my vintage desk for the next four months.

2. Did you learn anything from this experience/or grow in any way(s)?

Yes! I'll expand on this with a pros/cons list:

PROS of subjecting myself to this grueling gauntlet of Internet-initiated dates:

  • I no longer feel like a high-class hooker when I go to meet strangers in public places. Stare all you want, curious/judgy onlookers - zero shame over here.

  • I met some really nice dudes! Some I'm still friends with, some I still have inappropriate dreams about, and some were just lovely to cross paths with on this awkward journey we call life.
  • I learned that 8/8:30 is an age-appropriate dinner time in this city. No more 9:30/10. Unless you want people to think you're 24. The whole, I'm-just-trying-to-fit-more-of-my-own-single-life-into-my-day-before-squeezing-in-this-date-with-you thing is not an explanation that makes guys want to marry you. (Sorry, Mom, I will try to be less comfortable/happy all by myself.)
  • I ended up with a boyfriend! Now the world can stop asking me how on earth I've never had a bf and stick to asking me how on earth I'm still single.
  • I learned that there are a lot of really nice guys out there on the Internet/in life in general. Could I have learned that without this experiment? Sure, probably. Would've I? Probably not. There are many, many, many creepers and douchebags to sort through in order to find the nice guys. My notably low tolerance for all things shudder-inducing would have led me to abandon all apps at the first DTMO***. I spent probably somewhere between four to eight hours a day swiping and scrolling to excavate a, for the most part, pleasant lot of manner-minded men. You can't really do that if you have a real job, but that shouldn't rule out anyone still reading this.
  • I got gifts! Spotify playlists, restaurant recommendations, P-90x .mov files...I may have lost a small chunk of my soul, but I gained many, many life enhancers.
  • I learned a lot about myself. One of my favorite realizations was that I definitely have a first date sales pitch. And, boy, do I have that sucker down. Now if only I could live up to those buzzwords.
  • Forcing yourself to go on dates can actually be a really great thing. The problem with being totally okay with yourself/by yourself is that it makes it really easy to be lazy/not put yourself in potentially uncomfortable situations. Even the worst dates I went on had lasting merits. Read: Blog. Fodder.
  • I talked to so many strange men! For me and for many of my friends, years and years of being creeped on by skeezoids have resulted in a reluctance to acknowledge any approach by strangers of the opposite sex. Online dating takes the pressure off/gives us back a little control - if the initial convo gets weird, we can get out at anytime without explanation/abuse/or apology. Not to mention that handy little block button.
  • I learned that a third-night stand in Manhattan Beach will always be a little disappointing. This may sound like a negative, but I think it's something every girl should learn at some point in her life.

    • It's exhausting. I'm probably stating the obvious here, but a date a day is a lot. Even if you're mildly employed. Mostly because I apparently get schmammered on all of my dates. Remember that part earlier where I said I'm not 24 anymore? Social drinking now requires a very reclusive recovery - a recovery that lasts longer than 24 hours/isn't solved by a Bloody Mary brunch. Jumping right into dating a self-proclaimed functional alcoholic didn't really help the whole cringing liver/loss-of-brain-function situation either.

  • It eats up a lot of time. Please see PROS: #5. I stopped talking to almost all of my friends during these thirty days. Which made drumming up hilarious screenshots/content later much harder than it should have been. How did I not fwd that spectacularly creepy Tinder convo to anyone?! Oh, because I was too busy nestling up in fetal position/attempting to pick up strange dudes from the comfort of my bed. My bad.
  • It is a little weird. TO's break-up declaration wasn't wrong. I'm overly honest/have a totally monogamous nature - to the point where I generally have trouble dating more than two guys in the same month, let alone eighteen. I found myself white-lying about my evening activities on more than one occasion and feeling not wonderful about it. On this note, the temptation to create a fake life story is definitely strong when it comes to online dating. When you have zero connection to a person, what kind of obligation do you have to keep things honest? Isn't it much easier to tell them you're going spear-fishing in the Cayman Islands for a week than to be like, sorry I'm going to be having liquor-fueled heart-to-hearts with nine other men in the next seven days, so I'm going to have to ask for a rain-check on this date situation. Even if you're a grown-up and can say that to a guy (I'm not/can't), who's to say he's going to act like a grown-up and take it in stride. (I like to underestimate all of the men I date, because I hear lower expectations lead to higher highs.)
  • You don't know anything about these people. If you can construct a new personality, so can they - and I don't necessarily mean in a malicious way. Everyone wants to present their best (read: fantasy) side, but sometimes it would be helpful to have a little bit of that friend-of-a-friend background intel.
  • I'm sure this list could go on for days, but I'll leave it right here because the pros greatly outweigh the cons, and I think that's a fairly accurate assessment. I'm glad I did it. I absolutely recommend a less manic version - unless you're a totally manic person, in which case, please - follow in my delicate, generally pointy-toed, shoe steps.

    3. Damn it. I always forget to have a third.

    (For a mini little site-specific recap, click here.)

    *Not his real name
    **I hate the phrase 'intimate dinner', but this one really was that cheesy/lovely/may as well have been the cover of Montecito Magazine.
    ***Those of you who know me might be like, "But wait, I thought making out was one of your favorite hobbies?" It is. Only I prefer mine to be with a stranger I just met in the very real corner of a very dirty bar I'm so embarrassed to be at I won't even bother to steal the matches.

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