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.

#54 You’ve got to be kidding me.

Last night, I was texting with Bumble Virgin and he revealed to me that he was in THE NAVY FOR 6 YEARS. And the “longterm relationship” he was referring to was from high school. As I mentioned before, he’s not technically a Bumble virgin because I’m the second girl he’s met on Bumble. The first? They dated for 9 months! From where I’m standing in my shit pile of failed third dates, I’m simply amazed by those incredible odds.

I knew I liked him more than Queens Guy and I kneeeeeew it wasn’t going to be healthy, but my god, I was not expecting ANOTHER military man. Do they have military pheromones that I just can’t resist? WHY.

I had previously told him I’d share a good Bumble story in exchange for his story about his self-coined “unusual path,” so I told him the cliffnotes version of Army Spy, including the latest terrorizing. And now he’s trying to guess Army Spy’s identity! Because he apparently has a big profesional veterans network here and “would likely know the name.” He already weirdly knows my first ex boyfriend, so I reeeeally don’t need him establishing connections to anyone else from my regrettable past. No matter how ice cream drunk I get, I will not name names.

Speaking of exes, last night I also found out that my other ex (the one I loved, the one who mattered, the one I still like and respect) has had a girlfriend for some time now. That’s great, and I begrudge them absolutely nothing, but it did stir up a weird, 15-minute wave of ye olde emotions. And what that wave did was put into perspective how insignificant both Army Spy and Mr. Pineapple were in the grand scheme of love and life.

So yea, happy fuckin’ Tuesday.

P.S. I’m getting dinner with Queens Guy tonight.


After three weeks of A LOT of pretty flirtatious texting, I finally saw vaLLeyBoi818 on Sunday. We went for tacos and drank beer in my backyard. Then we made out and he had to leave. We might be doing something this weekend, but I can’t shake the all-too-accurate feeling that he’s lost interest. Whatthefuck-ever.


Two weeks ago, Pineapple slightly redeemed himself by officially ending our situation:

“Hey—we talked about ending things directly rather than letting them fade. You’re wonderful and I enjoyed getting to know you, but for me it’s time to move on.”

I responded with the classic,



I’ve never had much luck during summer (I can only assume it’s because I’m too intimidatingly tan and beautiful), so perhaps you won’t hear a ton from me in these coming months. Happy trails to you!


Coworker’s Friend seems to have lost interest just as fast as things were moving (3 dates in 1 week). We made dinner at his apartment on Tuesday, and got to a point where I had to inform him that my pants weren’t coming off (Diva Cup). Everything seemed fun and normal, but then the next day there was a drastic falling off in our texting, and we didn’t hang out this weekend while he dog sat, like he said we should. The fact that this all happened immediately after he saw me without a shirt on is disheartening. Cool! Oh Well!

I was supposed to see Valleyboi818 on Saturday, but he got sick. We won’t be seeing each other until Memorial Day Weekend since I’m going out of town next weekend and his weekdays are busy this month. He’s very fun to talk to and I’m excited for a second date. I am, however, prepared in case he ends up being a fuckboi, because he seems like maybe he could be. But right now, I don’t care.

Speaking of fuckbois! Pineapple texted me to neither hang out nor have a real conversation. Waste of my liiiife. If only deleting someone from your phone worked to send them an actual notification of deletion. I totally should have kept his airplant.


Everyone wanted to hold my hand this weekend, eczema and all.

I’m back from Cuba, where I befriended a 22-year-old, the-best-dancer-ever Cuban model. But we’re taking things slow. Like, no besos slow. Sorry to disappoint.

Before leaving for my Cuban adventure, I started talking to two guys on Hinge. I have since met them both: two dates with my coworker’s friend, and one date with Valleyboi.

Coworker’s Friend: 31, so obsessed with music and yet doesn’t even care that I physically can’t answer the question, “so what kind of music do you listen to?” He’s a bit awkward (but so am I 65% of the time), but he’s super sweet and funny and he somehow managed to kiss me on the subway (my least favorite locale for that activity) without making me cringe. I’m going to his apartment for dinner tomorrow, but so is my Diva Cup.

Valleyboi: my age, my area code, and we were talking about poo long before we met in person. After two CF dates, I wasn’t particularly excited about this one, but he surprised me. Very smart (in med school), very funny, with an unexpected dose of sex appeal. Tentative plans to hang out on Saturday.


Pineapple, WHO??

Mr. Pineapple went to Peru to take ayahuasca while I was gone and he should be back now, but I doubt I’ll hear from him and I don’t even care. Because going down on a woman is table stakes, dude, and we ALL need to remember that.

#47 Relationship Status: It’s Complicated

Mr. Pineapple came back a couple weeks ago and we’ve seen each other twice. But let’s back up a bit.

Before he left, we’d hung out 9 times, and I ended up asking him if he was dating anyone else. He said no, I said no. ‘Twas a brief convo. He left, we talked a bit, I sent him a postcard. He came back! And so did my need to ask the big questions and figure shit out. (Also, he totally saved my postcard.)

I never really wondered about “us” while we we’d be hanging out, but it plagued my brain when we were apart. So this past Friday after dinner, I worked up the courage and sweat glands to ask him to settle my confusion. I told him some things I’d been thinking (“I like you, this is fun, I wanna keep doing this, and I’m curious to know where you think this might be going”), and then made him share his thoughts with me—something he’s never ever done, hence my confusion. He told me he’s still figuring out his life ever since he moved here in July and got laid off in January and went soul searching in March (all fair points), and that he’s not sure if he wants a girlfriend or if he wants to date around or what. In fact, it turns out he is dating other people—though not yet sleeping with anyone besides me. Hoorah. I’m glad I asked, and he said he’d tell me if he does sleep with someone else. (And then obviously I’ll stop sleeping with him, but he doesn’t know that yet.)

Overall, the conversation was very good and healthy and productive, as miserably uncomfortable as it made me feel. Seriously, it was just what the doctor ordered. We continued our plans for the night and were able to have even more open conversations as well as a lot of fun, but in the morning I couldn’t shake the feeling that something was now irrevocably off. I told him that I’d leave it to him to reach out to make plans once we were both back from our respective travels in May, and he affirmed that he knows the ball is in his court. We’ve texted a bit since, but I’m stopping all initiations from here on out.

I felt nauseated and numb all weekend, and while I was drunk and hungover a lot, this felt like something different. It’s not that I thought he was my boyfriend, but I thought there was something there. Even if there was, I’ve learned that it doesn’t really matter as long as the dude is going through some internal shit (see: Army Spy).

So, now that my feelings for Mr. Pineapple are slightly shattered and I might possibly never see him again, I got back on the apps and have started talking to two guys from Hinge (each of whom knows a different friend of mine). Also, I’m on a soccer team with a pretty cute Midwestern guy who lives 15 minutes from me. :D

Besides, Mr. Pineapple is a Taurus and let’s all remember that last year I got a palm reading that said I’ll have one major love a little later in my life that will be “worth the wait.” I’m not expecting to meet him until my 30s, and I figure dating all these bozos in the meantime is great preparation for when I finally do.

Settle in, team, because I’m baaaaaack!


I’ve been out with Mr. Pineapple two more times in the past week. I should also mention that he knows he’s Mr. Pineapple because he’s the first guy I’ve told about this email thread. I really tried not to at first, but my coy vagueness could not keep his questions about my creative writing pursuits at bay. So, on our last date, I awkwardly told him about this, that I’ve purchased the URL (haiiii), and that I’m trying to figure out how to (and if I even should) evolve this. He didn’t run for the hills (perhaps because it was raining at the time), instead joking about how he was live tweeting all our dates. He’s pretty funny.

If you’ve seen my Instagram, you’ll have seen that we ended up at a bar that offered free shots if you could prove you were on a Tinder date. The only problem was that Mr. Pineapple had deleted his Hinge profile, leaving us proofless. So he launched into the story of my email thread as I prepared to pull it up on my phone for the bartender, and I think we were just so annoying and full of details that the bartender finally acquiesced. FREE SHOTS FOR US!!!!

In light of the fact that Mr. Pineapple knows about all of us here, I feel weird spilling every juicy detail, so I’ll just leave you with this: We made out.


I had two more dates this past weekend, and 2017 is starting out as a year where I only date younger men. *shrug*

Friday night’s date was very nice and talkative, a real pleasure to be around. I’d go out with him again, but I also worry that that could potentially lead him on. He was actually really trying to get me to invite him over to watch Gilmore Girls, but I don’t have a couch and Gilmore Girls is ME TIME.

Saturday’s day date was a mere hour and a half, and I think he might be the man version of me. We’re both from LA, we’re both Jew-ish (naturally, being from LA), we both speak Spanish (again, LA) and we bonded over gardening / practical botany. He told me about how he once grew a full-size, delicious pineapple, complete with photographic proof, and I immediately swooned. We are attempting to make plans to see each other again but he is a painfully delayed texter.