Dating : 50 First Dates

50 First Dates

No really, 50 literal first dates. And not in the cute Drew Barrymore hit-her-head, rom-com kind of way.

I’ve always figured, dating is a numbers game, right? If you date enough people, you will surely find one that you like (and add in a few more dates, and you’ll find one that likes you too!). Of course, we’ve all been taught “you gotta kiss a lot of frogs.” If you kiss enough slimy little amphibians, you’ll find your prince. Let’s just put it this way, I have dated all through the swamp, and while I haven’t found any secret royalty, I have come up with some absolute comedy to share with you all. Now sit back, pour yourself something tall and strong, contrary to the majority of men on this list, cause you’re gonna need it to get through this.

Oh, you’re wondering if I have a list of everyone I’ve dated? You see, starting in 2017 I decided to really “go for it,” say yes to dates, and see where it got me. It’s gotten me here, to writing a blog about dating. To be fair, that wasn’t my intention. But thank god for the list cause who has time to remember 50+ guys??

Note: Names have been removed to protect the underwhelming and for readers to not judge me for how many Chris’ I’ve dated. Instead they will be identified by the location (let’s be real, bar) of our first date. Now you can judge me for how much I drink instead.

1. Smitten Ice Cream — Starting this list off deceptively strong. Really nice guy that almost got me into Game of Thrones. Almost. Didn’t stick around long enough to even get me through one season.

2. Monaghan’s — Had a huge crush on him in college. After growing out my identity crisis fringe bangs and shedding my college weight, he didn’t recognize me, but it felt like redemption nonetheless.

3. Sabrosa — Are you even dating if you don’t test the water with your roommate’s friends?

4. Kozy Kar — Honestly, why I ever said yes to a first date in a bar that plays old school porn on the TVs and has a water bed, I will never understand. But he designed hiking shoes and that was fun.

5. Palmer’s — He showed up late to the date, was blacked out, and asked me the same questions again and again. The best part? He sent me a 3 minute long apology video the next day of him playing Hallelujah on the piano with the caption “well, Hallelujah for meeting you!”

6. Hawaii West — Met someone a bottle of wine deep on a party bus in Napa. Unfortunately, the wine goggles came off when we returned to the city and the romance ended as my hangover settled in.

7. ??? — Honestly have no idea who this guy was. Let’s just say this Chris didn’t pan out. There are a few of these.

8. Absinthe — You don’t shit where you eat. So don’t date guys in your office building. You will see them all the time. You will mutually ignore each other every time. It is unnecessary.

9. Silver Clouds Karaoke — Karaoke bar? What could possibly go wrong?! We will hold on to this one fondly though and always remember him as being the tallest, most attractive man on this list.

10. City Beer Store — As much as I tried to tell myself that I could date a dairy-free vegetarian, I’m truly not sure we ever had a shot.

11. Tacko — Similar to wine country brain, rooftop rose parties will quite literally have you wearing rose colored glasses. Until you sober up and realize that he’s wearing distressed white jeans.

12. Tupelo — Very wholesome beginning, met in a park, shared a few beers, hung out with his roommates, saw that he had a bucket hat that was covered in cats (see below). Definitely the one who got away.

13. ???

14. Esperpento — I thought meat and cheese were surely the way to my heart. This Spanish tapa date didn’t quite pan out, but I’m sticking to my theory.

15. Tacolicious — Honestly, I remember nothing particular about this date except that it apparently went no where

16. Marengo — Honestly really liked this guy. Got a little spooked out when I learned he did a cappella and drag shows in college, but he called it off before I had to really address those concerns. Makes me wonder, what red flags do I have that are more glaring than those?!

17. ???

18. Finnegan’s Wake — This was great! Great, of course, until he mentioned that he hadn’t totally ended things with his girlfriend in Chicago. Too bad, I really liked his dog.

19. Delarosa — The classic study abroad crush who was visiting SF for a week. Only took 5 years, but I finally accomplished 20-year-old Kelli’s goals.

20. ???

21. Park Tavern — Really hyper. Like whoah hyper. Still stresses me out thinking about how hyper this guy was. I was willing to get past the energy (and trust me, I’m not exactly low-energy myself), but I couldn’t get past the fact that he wore toe socks EVERYDAY. Talk about a nonstarter.

22. ???

23. Mauna Loa — Who knew you could ever make a meaningful connection at Santacon? I guess that shouldn’t come as a total surprise, I mean, day drinking and Christmas are my two favorite things in the world, so it really only makes sense that love was in the air.

24. Nook Café — Interesting-enough guy with a weirdly short neck. Things seemed promising after he cooked me homemade gnocchi while we watched SuperTroopers and he told me an elaborate story of disassembling a Pop-A-Shot to get it in his living room. Unfortunately, things came to an end shortly thereafter.

25. Barrelhead Brewhouse — I would have been so excited to date this guy in college. And he would’ve made a great 19/20 year old boyfriend. Sadly, he was 27 and that behavior is no longer endearing. Shoutout for getting me a hungover Gatorade though, that romance is real.

26. Neck of the Woods — I was promised steak. I was promised a steak dinner. I never got a steak dinner. I am still sorely disappointed.

27. Monaghan’s — Pro: insisted on taking me home (less than a mile) in a luxury Uber. Con: he got out of the aforementioned car and wouldn’t leave. Even when I put my retainers in and said something super subtle like “you should leave now.” Or when I took this picture to send to my best friend.

28. Modernist Private Club — Pretentious Mike! Should have known that anyone that takes you to their member’s only whiskey bar to sip on their personal, private collection is going to be subsequently referred to as “Pretentious Mike.” I am so proud to say that I consumed hundreds of dollars of fine whiskeys and thought they all tasted like legitimate ass.

29. Eno Wine Bar — I had an existential crisis: if you’re dating someone that works at a dating app company, are they really dating you or are they just doing market research?

30. The Lark — The entirely tattooed upper body freaked me out, the clucking noises he made at his cat disturbed me greatly, but his favorite pizza type of chicken and pineapple was the absolute deal breaker.

31. Local Brewing Co. — Great date, nice guy, texted me afterwards something about Harry Potter podcasts, and was subsequently gone for the next 3 months. It fizzled.

32. Absinthe — Do you ever wish you could will yourself to like someone that you’re not attracted to? That was this one.

33. Liquid Gold — He smelt really strongly of fish, kind of looked like a fish, had a picture holding a fish. One fish, two fish. Just too much fish.

34. Palmer’s — “You shouldn’t feel like you need to go drink-for-drink with me,” he slurred as I ordered another drink and drank him under the table. “I am denser than you can tell,” I declared as he only somewhat successfully tried to pick me up. Class act.

35. Blue Bottle Coffee — Hyper. Really hyper. Entire first date was spent discussing his upcoming trip to the police station to recover his stolen possessions from a recent robbery by a drag queen crime ring.

36. Nick’s Crispy Tacos — As I’m on my way to the date, he reminded me to bring cash for drinks and then showed up wearing a Budweiser Christmas sweater (in March). The next day he sent me a picture from Chick-fil-A in a Dr. Seuss sweater. Guess I can’t be all that surprised that he didn’t have a job.

37. Fat Angel — I can’t even think of something funny to say, it was just wildly unremarkable.

38. The Blue Light — My pen pal! Ever try and fail multiple times to go on a date with someone from a dating app and end up feeling like they’re your pen pal? This virtual friend hung around for 4 months in my inbox. Thank goodness for random nights that end at the Blue Light to kiss your hot pen pal, just to go back to our exclusively text exchange relationship.

39. Blackbird — Cute photobooth date #2 (right) as evidenced below. Went on a few dates, met his friends, got that “I’m-never-gonna-hear-from-him-again” feeling, and never heard from him again. Really glad that I never completed his $11 Venmo request for beer.

40. High Treason — How much time do you have? He must have a lot, cause he sure wasted mine. Would disappear for a month to text me how much he missed me, to half make a plan to then disappear again. His dog was really stinky too.

41. Cobb’s Comedy Club — The date that actually wasn’t a date. But maybe more of a proposition to join his Burning Man camp and/or therapy session about his somewhat-ex-girlfriend.

42. The Fish Bowl — When you meet someone named “Chris Brown,” can you afford to not date them? Pictured:

43. Crafty Fox Ale House — We met at a house party and he told me he liked my pants and that I have nice teeth. I guess I’m easy to please after all.

44. Robberbaron — Party boi. Like really fun, but you-drink-more-than-is-sustainable-for-a-relationship, party boi. Plus he asked for three subsequent rainchecks, which we all know is really just a rain out.

45. Fool’s Errand — Rings. So many rings. Why do I find it so unsettling that a man had on multiple pinky rings? I’m not sure, but it felt warranted.

46. Harper & Rye — Could have just been an averagely unremarkable date, but he delivered one of my favorite lines of all time: “I am going to touch your butt when you stand up, if that’s okay?” No.

47. The Social Study — If you can’t make a Quidditch joke when you’re on a date with a British ginger, is it even worth it?

48. Barrelhead Brewhouse — Didn’t actually live in SF. Wasn’t actually a dentist. Did, in fact, bring me a travel-sized toothbrush/toothpaste combo and talked about Scientology.

49. The North Star — He was covered head-to-toe in glitter and had a very recent cut across his nose. We talked about my favorite Instagram account, @thekurgerbing, so I thought maybe I had found the one.

50. The Wine Jar — Non-ironically used “#vegan” on his Instagram pictures. When asked “pancakes or waffles?” he responded “granola.” Do I need to say anymore?

Thank you for taking this journey with me. It has been a long road full of small talk, awkward hugs goodbye, and apparently a healthy tour of the bars in SF. Despite the underwhelming conversations, the texts that never came, and the downright alarming (looking at you Toe Socks Guy), it’s been a great learning experience for me.

Pre-date jitters have been replaced with confidence in my ability to talk to literally anyone. The past few years have taught me invaluable lessons about what I am looking for in a boyfriend/lover/partner and even more about myself. And while my numbers game theory hasn’t proved itself yet, I have some funny stories to entertain me in the meantime. Here’s to the next 50 and for everyone that has come along for this ride.