#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.

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