Tag Archives: dating story

Dater X: “Can I Ask You A Serious Question?”

Dater X: "Can I Ask You A Serious Question?"

Life is full of surprises: maybe you get pregnant without trying, win the lottery, find faith or cheat death. Other times, it’s the small, simple unexpectancies (I’m aware that “unexpectancies” isn’t a real word, but it should be) that make all the difference. Over the last few weeks, Baby Face has been my pleasant “unexpectancy.”

Having reconnected after five (or is it six?) years without a trace of contact, Baby Face and I have been spending a lot of time catching up, becoming reacquainted and starting back at square one. A lot has changed since our reckless beer-funneling college days, and not just because we’ve graduated to fancy craft beer and real glassware. Back in the day, Baby Face and I were friends, but we were never confess-your-deepest-secrets, share-your-embarrassing-stories kinds of friends. Last week, I was able to see Baby Face twice—once for lunch in the city and once for dinner and drinks at my place, where we were able to really talk and get to know each other, sweatpants on, makeup off and all. Keep reading »

Dater X: The Best Sex Of My Life

Dater X: The Best Sex Of My Life

Excuse me while I wander around the lovely landscape of cloud nine, because I had the best sex of my life this weekend and I’m still up here enjoying the high.

So, let’s bring it back a week. After my grandma passed away, my communications with Baby Face became more and more frequent. Before our date/catchup/death dinner we’d text each other a few times a day to flirt and shoot the shit, but since then things have certainly accelerated. We chat in the morning on our commutes in to work, briefly throughout the day via text, and almost always in the evening before bed (sometimes there’s even an actual phone call, which I love). Mid-last week, Baby Face asked me if I wanted to go out with him and a couple of our old college friends on Friday night after work, but I’d already made plans with some of my girlfriends. We decided to compromise and hang out with our respective pals individually, and then meet up later in the night, with or without the others. Keep reading »

Dater XY: Did Chemistry Ghost Us?

Dater XY: Did Chemistry Ghost Us?

They come few and far between but we all have them. You know, those first dates that make you think, Wow, is this the one? I had one of these dates last Tuesday with The Lawyer.

We met at my favorite watering hole and jazz club for drinks. We arrived at exactly the same time, an obvious omen of good things to come. Continuing on the good omen train, while looking over the wine menu, we found out that Malbecs are our favorite type of wine. Keep reading »

Dater X: Death On A Dinner Date

Dater X: Death On A Dinner Date

Unfortunately, I’m becoming a professional at going on great dates that have awful endings. There was my first date with Scar Twin, which went off without a hitch until I fell down a flight of stairs; my first (and last) date with Jack, who wrapped up our evening by insinuating that I’m a slut; and most recently, my great — and also tragic — date with my old college friend Baby Face. Confirmed: Tears do not taste good in dirty martinis. Keep reading »

True Story: I Dated A Sociopath (And I Liked It)

True Story: I Dated A Sociopath (And I Liked It)

I spent most of my late teens and twenties the way a lot of girls/women do, flip-flopping between the guy who couldn’t find his self-esteem with a military-issued navigational system and the guy who was so self-centered he never went down on me without expecting six blowjobs in return. When I hit 30, I needed a change. Then I met James.

I had written prolifically online about my love life, especially the failures. And from the beginning, I knew James had read it all. I didn’t think much about it until I noticed how often our goals, beliefs, and sexual proclivities matched up. I thought I had hit the jackpot. How did I find the one guy who not only believed in handwritten love letters, but also had no problem fucking me so hard I couldn’t walk for two days? He was handsome, brilliant, and had that Old Hollywood charm. He seemed perfect. Too perfect. Seeing as I was not a delusional Disney Princess, that made me examine things more closely. Keep reading »

Dater XY: It’s In Her Kiss … Or Not

dater xy kissing

I mostly use Tinder to pass the time on the subway. But about three weeks ago, I matched with The Marathoner. Given the information provided in one’s Tinder profile, all I knew was she enjoyed running and was highly attractive. She sent me a message asking about the Charles Dickens’ quote I had in my profile; the next thing you know we had our first date planned. We decided on going to a local brewery that was having a bacon party.

We shared a few flights and enjoyed lots of bacon. We talked about the usual first date topics: our likes dislikes, what we do for a living, etc. I’d said it went very well, as far as first dates go. We had good chemistry and she seemed like the type of woman I was looking for; fun, intelligent, athletic, and attractive. When it came time to part ways at the subway, I asked her out on a second date and she said yes. Keep reading »

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