#95

Remember the Older Dude from the Circular City Week events, with whom I drank to escape Phabio? (By older, I was assuming early 40s.) He and I professionally kept in touch, and got coffee a few weeks later. Then, in May, he invited me to grab day drinks in our neighborhood. Unlike my friends, I wasn’t sure if he meant it as a date; but just to be clear that it wasn’t, I wore no makeup and told him I had to go grocery shopping afterwards (which I did!). Despite a lower-back-touch that I had to quickly wiggle away from, and a declined invitation to continue drinking on his roof, I think I did a pretty good job of establishing our friend zone. I deflected a few follow-up invites, and then didn’t hear from him again until he asked me to get drinks last weekend. He’s cool, and I assumed our age difference was enough to solidify the friendship boundaries, so I accepted. (His age has since been confirmed as 46.) Unbeknownst to him, we met up after I’d spent the afternoon drinking multiple tiki drinks at my friend’s party, but I think I managed to come off as deceptively sober. After two cocktails that I definitely didn’t need, he walked me to where I was meeting up with some other friends. He left, and we girls got ice cream! It was a perfect day of friendly socializing.

The next day, he texts me:

Nice to see you last night. How was the rest of your night? So, the few times we’ve met it’s been in this somewhat professional zone. However, I’d like to take you on a proper date sometime. You’re lovely company :)

Before you say “aww,” you should know that he has a roommate—an automatic loss of points for anyone trying to date me. Plusssss, I have the rest of my life to date 40-somethings—and only an ever-shrinking window to cradle-rob 20-somethings!

I responded:

That’s very sweet, but I have to decline. I’m interested in someone else right now.

He said:

Understood!

And that was that!

Who am I actually interested in? The Psychiatrist (31), who won’t text me back or make plans to see me again—of course!

#94

This past Friday, I went out with the psychiatrist I met while #dancingonmyown. We had texted sporadically over the past 5 weeks (mostly him initiating—ha!), and he finally asked if I wanted to get a drink when he came into the city for a haircut and a change of scenery as he studies for the boards. I had already scheduled a bikram class before our date, and I only had time to shower before meeting him, which means I was fairly dehydrated and hadn’t eaten since 2pm. He chose a bar for its live music (woof), but it ended up being a surprisingly great time. When the music ended, I’d had three beers (and water!), and told him I had to stop drinking and start eating. He suggested I also start smoking, so once again we ended up back at his friend’s abandoned apt (which he cleaned!!!) to smoke, listen to music, and eat pizza.

Every smoke session is a roll of the dice with me, and this time I was decently awkward. At one point, I played Pizza Day by The Aquabats for him, which killed any semblance of a mood (at least for me, haha). He didn’t try to kiss me until right after the pizza arrived, and I had to shut him down after less than a minute because I was starving. Aside from correctly guessing many elements of his birth chart (double Virgo, Venus in Cancer), we didn’t get too intimate and I eventually went home.

Reflecting the next morning, I felt unsettled by the fact that we hadn’t “progressed” on our second night together (in fact, I’d say we regressed), and I got anxious about whether or not he would text me. Reflecting on THIS, I realized that I’m not used to *not* rushing into sex, and I subconsciously assume taking it slow (which is apparently more than 2 dates) hurts my “chances.” Chances for… I’m not really sure what. Sex? Love? Maintaining their level of interest? I had apologized when I stopped our makeout, and he told me I never have to say sorry for that—[pause to swoon]—so, logically, I’m not worried; but psychotically, I’m convinced I “messed up.” As a supposedly progressive, feminist woman, all this introspection has been quite the mind-fuck—especially when all I’ve been wanting for the last 6 months is a body-fuck. Or have I???

If I do see him again, would it be inappropriate for me to lay all this on him and get some professional feedback? :)

#93

A few weeks ago, I went on a strange first date (he asked if I was an artist, if I considered myself a hipster, and if I’d ever run away from home). That more or less finalized my decision to deactivate my Hinge account, and I am now officially off all dating apps, with no plans to sign back up. It feels great!! Leading up to this, all I had been doing was sporadically talking to a few guys that I wasn’t even excited about. In fact, when one of the odder ones suggested we meet up, I unmatched from him rather than agree to a date I knew would be miserable.

Little did I know I’d run into him at a bar while out with my friends this weekend! LOL. We had literally just arrived when I squeezed into an open spot at the bar to fetch us all drinks. The guy on the adjacent stool started talking to me (he said my “sorry” didn’t sound very genuine, and I told him he was right), but I was trying to make eye contact with one of the bartenders and order. I could feel him staring at me, so I made a bit of conversation while I waited for our drinks, and then moved away from the crowded bar as soon as I got them. Back with my friends, I told them I was pretty sure I had matched, chatted, and unmatched with the guy at the bar. We chalked it up to a kooky coincidence and allowed ourselves to be approached by the many other male bar patrons. A little while later, the same guy from the bar/Hinge approached me, said I looked familiar, and asked if we knew each other from somewhere. I told him we had matched on Hinge; he remembered me, and how I unmatched him (lol). I told him I actually deleted my entire profile, skirting the fact that I had first deleted our match. As usual, my instincts were right! After politely conversing for a few minutes, he could not pick up on the hint that my friends and I wanted to hang out without him, and he proceeded to awkwardly linger and STARE AT ME, neither attempting to make conversation nor leaving us alone. As he fiiiinally finished his beer, my friend asked if I wanted to join her at the bar to order more drinks, and I agreed, fully ignoring and leaving him behind. The move was a lie, and my friend confirmed he left the establishment as soon as we walked away, leaving us all relieved to be free of the dually dull and creepy cockblock. Hooray!

#92 Oh, What a Night

There was a Scorpio full moon last night, and what a wingwoman she was.

I had been wanting to check out this monthly dance party at a nearby bar, so I invited a slew of different friends to ensure I’d have someone to go with. But, reminiscent of many a birthday party, nobody showed. Still, the moon had me feeling some type of way, and I knew I was going regardless. I leisurely pregamed, primped, and showed up around midnight, where I waited in line behind a guy who was also alone; though I assumed he was meeting people inside, like a normal person with friends (NOT ME, THANKS GUYS). But actually, thank you—I ended up having the best time, and I’m now convinced you’re all cockblocks! (Please still hang out with me though :))))))

I paid the $5 cover and ordered a Tecate (#ad). As I tied my jacket around my waist, a stranger tapped me on the shoulder and said I dropped this. He was holding a crumpled $20 bill. I told him I didn’t think it was mine, but he gave it to me anyways. So, despite having zero friends and paying a cover charge, the night was already profitable.

The party was bumpin’ and it was dark and crowded enough that I didn’t look crazy for being there alone. But really, who needs friends when you’ve got beer, a vape pen, and some funky beats? I was having a great time, but definitely being a full-on Scorpio creeper as I lurked in the shadows watching everyone dance.

After a while, I noticed that the guy from the line was indeed there alone, fully focused on the dj’s and strictly there for the tunes. *swoon* It became my mission to eventually get close enough to strike up a conversation and/or dance-off. While I was boppin’ and schemin’, a cute guy started talking to me. He was cool, and we went outside to hear each other better. It came out that I was there by myself and he congratulated me on valuing my time enough to do what I wanted, with or without accompaniment. I agreed and said, “on that note, I’m actually gonna get back to the party, but I’ll see you around.”

I went back in and got to groovin’. (I think it was at this time that a girl got on stage and started dancing with her top off. #scorpiofullmoon!) I didn’t have to deal with creepers grabbing on, which was nice, and I politely declined one guy’s invitation to dance. I was on a mission, remember! At one point while I was off to the side, I could feel a guy near me working up the courage to make a move. He pointed out that we were both drinking Tecate and asked if I wanted another one. I said no thanks and he backed off. He was cute, but I actually didn’t want another drink (I had been intermittently refilling my can with water #stayintheblue). I felt a little bad about shutting him down so fast, and decided that if I ran into him again I would give him another chance. About 20 minutes later, he respectfully approached me while dancing. I really do not love dancing with guys, because they usually can’t keep up and/or just want to rub their dick on me, so it’s kind of a big deal when I allow a man to touch me on the dance floor. He wasn’t as bad as he could be (which I told him), and we were having a good time. Then we start making out, and my inner monologue just cackles away at how well my solo night out is going.

He lives on Long Island for his psychiatry residency (originally from LA), but was staying at an out-of-town friend’s apartment nearby. I hadn’t had a decent shtupping in almost a year (DCD), so I mentally prepared to see this ridiculous night through to its most Scorpionic conclusion. (I had even shaved my legs for the first time in many weeks thanks to the fresh spring weather.) We went outside for air and decided to go to “his” place for weed and Artichoke pizza. I made him promise not to murder me (doctors make the best killers after all), and texted a friend my whereabouts because safety first! He apologized in advance for how messy it was, and thank goodness he did. As we smoked and waited for the pizza to arrive, I told him I couldn’t have sex in that apartment—no woman could—and to relay my feedback to his friend. [While I clearly didn’t mind having sex with Diet Coke Dealer amongst pounds of cat hair and a sink full of dishes, this place was waaaaaay too messy, the couch was uncomfortable, and I wasn’t going anywhere near the unmade bed.] He was nice and said he wasn’t expecting anything (even though I had been, sigh), and we chilled for about an hour until I went home, virginity intact, at 3:40am.

Remember when I said I had to stop smoking weed with guys because I get too weird? I’ve recently changed my tune on that, and think guys kinda need to see the high me to know and appreciate the real me. Can’t decide if that’s tragic or not, but it definitely allows me to be more “authentic.”

In conclusion, if you really want to go do something but don’t have anyone to join you, go fucking do it anyways.

#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.