#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.

#81

Diet Coke Dealer and I have still been seeing each other, although not as frequently as I had once hoped. Mercury Retrograde was a doozy, and had me going back and forth on whether it was completely over or if I should woman up and have The Conversation. Knowing that I’d soon be gone for 10 days of family vacation, I decided on Sunday that I needed some answers in case my Grandma asked if I was ever getting married.

After a delightful Crazy Rich Asians date (my plan, obvi), we were walking down my block when we were greeted by some very loud, very danceable West African music (a DCD fave) [I also don’t know what the exact genre is called, so apologies for being culturally insensitive!]. We could see there was a party going on, and the guy hanging out at the side gate confirmed. DCD asked if there was dancing, the guy said yes, and suddenly we’re in a stranger’s backyard being offered food and drink at what we later discover is someone’s birthday party. We were there for about an hour, where we danced (after I more or less chugged a few cups of prosecco), mingled, and forced some delicious Nigerian rice into our already-full stomachs. In classic DCD fashion, he wowed everyone with his dance moves, to the point where people were recording videos and asking where he was from because he couldn’t possibly be American. LOL

But the best part of our party-crashing was how every woman we met (all two of them) immediately asked if we were boyfriend and girlfriend, or married. We awkwardly responded “I don’t know,” and he asked if he was in trouble. I told him he wasn’t but that we’d obviously be discussing it later. Thank you, fairy godmothers!!!

When we got back to my place, I asked what all the Nigerian women were dying to know: “So, am I your girlfriend? Are you my boyfriend? What are we?” He said he didn’t know and that he’s hesitant to don those titles because he knows his level of communication is already poor, that being a boyfriend would raise those expectations even higher, and he doesn’t want to disappoint. Momentary disappointment aside, it was refreshing to hear him acknowledge his lack of reaching out, because it meant I wasn’t crazy. Once we moved past expectations and got into feelings, we both agreed that we like each other, we want to keep hanging out, and we’re somewhere in between full-fledged BFGF and sporadic-Hinge-dates. He said he refers to me monosyllabically as his “girl,” which is fine by me because I’d certainly rather be considered his “girl” than his “friend.” All in all, I’m pleased.

Finally, perhaps the most exciting update of all: on Wednesday, he washed his dishes.

#79

3 more weeks, 3 more sleepovers. Also, it turned out that neither of us are able to go to The Cape this week, so nevermind!

I presume everything is going fine, but sometimes he’ll go dark for days on end. I’m currently in a he-ignored-my-last-three-texts-so-i’m-gonna-remain-silent-indefinitely standoff. Last time, he texted after four days, and I felt extremely victorious for holding out. It also helps knowing that I am, objectively, the catch in this pairing. Or is that just what confidence feels like?

The thing is, he’s fairly irresponsible (occasionally forgets we have plans, or will ask to hang out day of), and I can’t tell if that’s due to a lack of interest or a lack of what I consider to be basic adult social skills. Not to mention the fact that every dish he owns has been sitting dirty in his sink for months. Nobody would ever consider me a clean freak, so the fact that I think he should toss the lot and give up on owning dishes altogether means something. At least he has cats to keep vermin at bay. And like, all boys are filthy and forgetful, right?

He said he wants to come to my student loans payoff party, but I’m not getting my hopes up because all of the above. Oh yea, I just paid off my last student loan. :D

TLDR: Per usual, I have no idea where I stand or “what we are” and there are enough red flags to keep me from asking, “am I your girlfriend?” So, limbo it is until further notice!