#91

I had two first dates last week that were both fun, but I don’t really care to see either guy again.

  • The first guy is a theater kid who’s obsessed with Starkid (and thinks I’m really cool for being associated with them) and karaoke, and tried to pressure/shame me into a Monday night karaoke second date. When he wasn’t running his hand through his own hair, he touched my knee a lot; then he walked me home but didn’t try to kiss me. All in all, I’m skeptical about his enthusiasm for vaginas.
  • The second guy was nice and funny, but a little basic. We went to a dimly lit champagne lounge (not.my.vibe) where we made out briefly, but he opened his mouth way too wide. I got duped into going further uptown, where he invited me to “watch something” at his apartment. I declined, we got food instead, and he was impressed that “unlike most girls,” I didn’t order a salad. Who orders just salad at a Thai restaurant?

I don’t know if I’ve maxed out my “luck” on dating apps after 5 years, but I think I need to stop going out with random strangers I meet online. Or maybe I’ll re-download Tinder first, just to be sure. Regardless, I fully intend on meeting someone at one of the many weddings I now have on my horizon—so to all my brides-to-be, don’t give your single guy friends a plus one.

#90

Remember when I said I wouldn’t be able to see Phabio anytime soon because I was all booked up this past week? Well, I was hobnobbing at a bunch of Circular City Week events, and it turns out life is super creepy because I ran into him at one on Thursday. Coincidence? Stalker? I just didn’t want him harshing my hustle or whatever-the-professional-version-of-cockblocking-is me. So we chatted and sat next to each other, but I made it clear I was there for business. (At one point, he asked if I wanted his help talking to people—which I found weird and condescending mainly because he has fewer ties to the industry than I do—and I enthusiastically declined.) Apparently we’d been at the same event on Wednesday (where I met a cool older dude with a professional quandary similar to mine), and we were both going to the closing celebration on Friday.

Last night, I was running late, and Phabio texted to ask if I was still coming to the event. I eventually got there, quickly said hi, and lined up to cash in my drink ticket—where I made some new connections. After emerging from three separate conversations, I made an effort to go find Phabio, but he was busy, so I made myself a pitiful dinner from the picked-over snack table. I was soon ensnared in a new dialogue, when he comes over and EATS A CHIP FROM MY PLATE WITH A SMIRK. I told him he’s not welcome to my food, and declined his request for a hug—all in front of the poor woman I was talking to. They start chatting, and the guy I met on Wednesday magically appears. Drink tickets have run out and he suggests we spend our money on legitimate cocktails at the hotel’s lobby bar. I agree and we skedaddle. We get our drinks and chat for a while before I leave to meet my friend. During this, Phabio texts me asking if I left. I respond when I leave, and he asks me to dinner next week. I decline and tell him I’m not feeling a romantic vibe with him. He says he picked up on that because I was rude to him (??), but also asks why. I tell him it’s a gut feeling, but he continues to ask if I’m open to a romantic possibility. (Not sure why if I’m apparently so damn rude!) I tell him no, and he asks if I’m hung up on someone else or if he’s just not my type. I tell him I’m not really in a dating mentality at the moment (which is true, in addition to the fact that persistent and insulting isn’t my type), and he thanks me for being honest and finally says he’ll step back but to let him know if I change my mind. Not likely.

#89

I went on a Hinge date last Thursday and it was fine; the highlight was eating pickled eggs. As soon as he texted a few days later, I told him I didn’t want seconds.

2 weeks ago, I went to House of Yes, and within 20 minutes of being there, a guy wearing ski goggles asked if I could put on his glow stick bracelet for him. My friend was already disappearing into the crowd, so I adorned him as fast as possible as he asked my name and told me he’d buy me a drink later. He eventually found me and came through on that offer. He’s Brazilian, objectively good looking, but I can’t take him seriously with a name that… “rhymes” with… Phabio. I didn’t want to hang out with him all night so I gave him my number and went off to join my friends. He lurked a bit, but eventually got the hint that I didn’t want to dance—especially when I told him I hate EDM. He texted the following week and asked me out. I was dreading the date, but it turned out to be not so bad. He was cool to talk to, an excellent gentleman, and very accepting of my hippie dippie ways. Also I found out he’s 35—which doesn’t matter, but was shocking nonetheless. Am i excited to see him again? Not particularly, but I figure maybe it’s worth a second chance.

Tonight, I went on a Hinge date that lasted 37 minutes. Not my record for shortest date (28 mins), but very close. Making conversation was a painful endeavor. Bleh, just blehhhhh.

And it all got me thinking. It’s one thing to be OTL (open to love), but lately I feel like I’m just going out with any dingdong that asks. Shouldn’t I be excited? Shouldn’t I be remotely attracted? I’m trying to give app boys a chance because maybe it’s not their fault their photos are bad, but also maybe I should just trust my shallow gut. I’m worried I’ve lowered my standards to dangerously low levels, and I think I need to be truer to my picky, judgemental self.

I’m proud of myself for making an IRL connection, but I’m not sure what I did to deserve it aside from wearing half a shirt and no bra. I’m all booked up for the next week, so I have a solid excuse for not seeing Phabio for a while. But if I’m talking like that, I probably shouldn’t go out with him again, right?

#88

About 2 weeks ago, I went on a third date with the long haired guy, and it was confirmed that we have no romantic chemistry whatsoever (we never kissed). We went to Barcade, and it was a nice reminder of how fun that place is. Who wants to play pinball with me sometime?

Since then, I’ve been on two dates with a chemistry teacher. Our first date was a Saturday night dinner, and I accidentally got very drunk—classic me! He was fun (but who isn’t when I’m wasted?) and we kissed at the end. Our second date was last night and he was 30 minutes late because he was playing a board game with friends. [I’m sure you can visualize my facial expression.] He made up for his lateness by monologuing and mansplaining all night, mostly about obscure science topics. On the walk home, he complained about how cold he was, and I told him to grab a cab if he saw one since we were walking in the opposite direction of his apartment. He insisted on walking me all the way home, and I suffered a brief, frigid kiss before running inside alone. Now that I think about it, he was also 20 minutes late to our first date. Needless to say, there will be no third.

Perhaps all the fun ones are currently cuffed, but I just can’t seem to get excited about any guy as of late. There is one new boy on my soccer team that’s very cute and very friendly (specifically to me, I think?), but I’m not sure what to do about it. I recently realized I’m only competent at dating when I already know the guy is interested (i.e., when he matches with me on a dating app), but I am 100% clueless and awkward when it comes to IRL interactions. I can’t flirt, I can’t detect flirting, and I definitely always assume they’re not into me. I feel like this is a life skill I need to develop in 2019, but I have no idea where to start. Please send help.

#87

1. The guy who likes pugs had to last-minute postpone our date (I was drinking with friends and did not mind at all), and I haven’t heard from him since. Woohoo!

2. LBD and I went to see If Beale Street Could Talk on Sunday night, and the adorable romance of the movie made it clear to me that we are nowhere near that level of chemistry. I think he picked up on my lackluster vibes, because I haven’t heard from him since. Shrug!

3. Last week, I went out with a guy with long hair—and I just got back from our second date (I’m a little drunk). I’m usually not into long hair AT ALL, and I’m still not sure if we have any chemistry (we haven’t kissed), but he is super funny and nice. For those of you wondering, his hair is about shoulder length, looks very clean, and is kind of wavy. When I asked if he ever puts it up, he said “man buns are the modern-day mullet.” I died laughing, and couldn’t agree more. Also, we ran into one of my old coworkers, who sat next to us with his friends for the duration of the date.

4. On a slightly more philosophical note, I think I’m not that interested in dating at the moment. The fact that I am in the midst of figuring out my career and trying to make sure I can pay rent (in case you didn’t hear, I quit my job) means I have very little patience for the average bozo. If a guy wants to chase me down and make me fall in love with him, so be it. I’m always happy to meet new people and have fun, but I definitely do not have the time or energy to devote to dissecting texts or wondering if a guy is obsessed with me. If he’s not, he’s an idiot.

#86

Before the holidays, I had an odd date at a fancy bar in Manhattan. I had come from watching my friend’s amateur improv show, and was feeling especially quippy. Throughout the entire date, I couldn’t tell if the guy was being sarcastic or not, so I responded with the full force of my sass. But he asked thought-provoking questions, and I’d say it was an overall enjoyable experience. On the walk to the subway, we discovered that we both love pugs. Then he surprised me with an extremely fast and awkward kiss—he basically pecked my tooth—and asked if I’d want to hang out again. I said sure, but was kind of hoping he’d forget. We have a tentative date tomorrow.  

After 4 weeks of not seeing each other, I got dinner with Literal Blind Date (LBD) this past Friday. After 4 months of not having sex, I had cleaned my apartment beforehand just in case. He came over after dinner, and the sex was… very polite. I’m not sure if it was due to lack of chemistry, him holding back, or my dry af, free condoms, but I actually thought to myself, “is this what bad sex is?” It made me nostalgic for Diet Coke Dealer (the passion, not the moderate emotional torture), and it reminded me of the lesson I learned when things ended with Mr. Pineapple:

Because he knew about these emails, I never shared many details about the sex I had with Mr. Pineapple—but it was pretty lame. He wasn’t into foreplay (he actually said that), the sex was plain, and he never made me orgasm. Then, the last night we hung out (after our big DTR conversation), he revealed to me that he’s actually very kinky and keeps a box of BDSM toys under his bed. Shocked, I asked why he’d been forcing us to have such boring sex with each other, and he said he didn’t want to freak me out.

I was still fairly inexperienced back then and didn’t necessarily know what I wanted, but that experience really drove home the importance of bedroom communication. I’ll obviously give LBD another chance—at his place, with his condoms, and whatever box of secrets he might be hiding—but I’m also prepared to accept that we might just not be compatible.

**In the meantime, can anyone recommend a condom they like? Clean/non-toxic options are preferred—but before you suggest Sustain, please see my scathing review of those in email #59.

#85

I ended up seeing Literal Blind Date on Thursday and Sunday. On Thursday, I pregamed our dinner date with my friend who was also going on a date and we accidentally had 3.5 beers each, so I was drunk upon arrival. Oops! But I think I played it cool. On Sunday, we met at a bar in Brooklyn for a 5pm meal and a rousing game of Scrabble, which I won. He’s going to Iceland with his mom on Wednesday (aw) and returns the day I fly home for Xmas, so we planned to reconvene in 2019. Famous last words? It sure as fuck wouldn’t be the first time. But our relaxed momentum is a welcome change of pace, and I have plenty of other things to fret over.

In other news, I think Mr. Red Socks was also not feeling the vibes, and I thankfully haven’t heard from him since.

#84

I went on a second date with Mr. Red Socks on Wednesday. We got tacos and went to a mezcal speakeasy, and he told me he voted for Mitt Romney (he “experimented” in college by trying out Republicanism). In the words of a wise friend: “Red socks, red scarf, red values, red flag.” Politics aside, it was a pleasant date, but I don’t think I’m feeling much of a spark. I think that’s partly due to the fact that…

On Tuesday, I had a very fun first date. Before meeting, our Hinge convo revolved around S Club 7, The Spice Girls, and Beanie Babies—already off to a very compatible start. I was running a few minutes behind and he waited outside the bar for me, which was oddly nice because it’s winter. The bar ended up being too crowded so we walked to another place down the block. The hostess of this dimly lit wine bar pointed us to a table in the back, and he seemed confused. That’s when he told me that he had gone to the eye doctor earlier in the day, and he still couldn’t fully see. I joked that he was on a literal blind date, and then realized I was now in charge of reading the menu for us. Our 4-hour date ended with a walk to the subway station and a brief, surprisingly good makeout. No idea if he actually knows what I look like, but we are going out again this Tuesday. TBD if he’ll get an invite to my company’s holiday party on Friday.

#83

I went approximately 6 months without going on a first date, which I believe is my longest streak since Tinder Tom popped my app cherry 5 years ago.

Last Monday, I went out with a Hinge guy (who knows the boyfriend of my coworker) on what I think might have been my most grownup date ever. I trekked all the way up to the UWS (I’m so nice!), where we got dinner and negronis at a lil Italian place, and then saw a jazz show even further uptown. I ordered an old fashioned and then a manhattan and was feeling fancy af. He walked me to the subway and we shared a delicate kiss goodbye. He seems nice and smart and funny, and he says he only wears red socks—quirky! He’s in China for two weeks, but maybe he’ll ask me out when he’s back.

I’m in no rush, and in the meantime am trying to figure out how to successfully slide into the DM of a very funny, very minor Instagram celebrity. Tips welcome!!!

P.S. Despite Venus Retrograde, I haven’t heard from Diet Coke Dealer, which I think is for the best.

P.P.S. How do you know if a couple you met at a dinner party is hitting on you for a possible threesome, or just genuinely wants to be friends? And if it’s the former, how do I successfully friendzone them?

#82

Diet Coke Dealer forgot that we had made plans to hang out on Labor Day, my saddest day of every year as I return from my San Diego vacation. I asked him to call me instead, and he said he would after dinner with his mom, but he never did. I didn’t hear from him at all that week. I called him that Friday night, and he didn’t answer that or the follow-up text I sent. On Sunday night, I texted: “If you insist on ignoring me, then I can only assume this is over.”

The next morning, as I was leaving barre class, he texted me. He said his uncle had a stroke and he went to Connecticut without his phone (I doubt the latter, but didn’t bring it up). He also said he hasn’t been doing well lately, and has been really sad and can’t seem to shake it. Having already experienced the Depression-Dumping on multiple occasions (see: Army Spy, Mr. Pineapple, Neighbor Boy), I thanked him for finally responding, wished him the best, and told him that I liked him a lot but understood this probably wouldn’t work out. He thanked me, told me he liked me a lot too, and said he hoped he could see me again. I told him I hoped for that too, but he’d have to be the one to reach out. He agreed. After a bit more texting and a lot more crying, I went to work. It was an awful day. On Tuesday, I couldn’t stop thinking about our 20-minute text conversation, how there might have been some miscommunication, and how I’d feel a lot better if we could talk on the phone. After work, I texted him (clarifying that this was not me reaching out, but requesting a continuation of the previous day’s chat) saying that I didn’t like having meaningful conversations over text and asked if he’d be open to a quick phone call sometime soon. It’s normal for him to take forever to respond—or sometimes, not respond at all—so I’m not getting my hopes up that he ever will. Either way, sending that text and asking for what I needed instantly made me feel so much better.

Diet Coke Dealer had the most red flags of anyone I’ve ever dated, and I know deep down we’re not supposed to end up together, so it’s probably best if he actually never reaches back out. Still, we had a lot of fun together, and I hope he can get a handle on figuring out his life. Also, I’ll miss his cats.

In the meantime, I don’t plan on re-downloading any apps until after I return from my solo trip to Finland in mid-October.