sex diaries

The Woman Afraid of Leaving Hickeys on Her Divorced Date

Photo: James Gallagher

This week, a woman seeing a divorced 30-year-old but thinking about an ex-hockey player: single, 25, Portland, Oregon.


12:00 p.m. I’m so excited to see H today after work! He’s an ex-professional hockey player and something of a golf fanatic — in other words, not the sort of man I typically like. I love a good manly man, the laconic type who doesn’t quite know how to get in touch with his emotions but offers such physical refuge that you’re almost able to forget that. I grew up in the Midwest, so I’m familiar with hockey players, and I recognized his smile the moment we met: It was a big, healthy smile that conveyed confidence, the love of a good time, and a dickish amount of man. 

I’m seeing three other guys right now, but H has risen to the top. When I’m in the act with B, I think of H. When I’m chatting with L, I think of H. When I’m laughing awkwardly on the couch with C, I think of H. H is 34, the same age as my ex, whom I dated for four years. H says he likes me because I’m communicative and straightforward, and so far he’s been nothing but the same with me — so unlike my ex.

2:00 p.m. H texts me a picture of a recipe for squash paella. “How does this sound for dinner tomorrow?” he asks. I text back immediately: “I thought we had planned for tonight?” I scroll back on our texts and see that I am not wrong — we made dinner plans for tonight. I have a sinking feeling in my stomach that he’s going to flake.

9:00 p.m. He still hasn’t texted back, but he’s been active on Match (which I downloaded to stalk him some weeks ago) and his Tinder distance has gone from four miles to 14 miles away. I have two drinks at a bar with my co-worker and head home.


2:00 a.m. I look at my phone because I can’t sleep and see that H has just texted: “I slept straight through last night. I wish you had come and woken me up, but that’s my own fault.” He was recently laid off, so his sleep schedule has been wacky. I decide to wait till morning to text him back.

8:00 a.m. I write, “I’m honestly pretty hurt you flaked last night, and I don’t appreciate your excuse. I thought our relationship, new and undefined though it was, was based on honesty and communication. If you’d like to apologize, feel free to drop a bottle of wine at my house tonight. Otherwise good luck with things.”

He responds immediately,  “I wasn’t making an excuse. I think we’re on two totally different pages and I’ll acknowledge now that you are probably right. I’m sorry, I don’t know what else I can say. I would like to get on the same page, though. I assume you’re busy tonight though.”

What a liar. If he thought I was busy, why did he make dinner plans for tonight with me last night?

8:15 a.m. “I’m free after 6:30 p.m.” I write. “Why would you think I was busy?”

“You told me I could drop a bottle of wine off. Obviously there are a lot of different things that led to this but we are not currently clicking. You tell me you’re free after 6:30, I feel like you don’t want to see me. I feel like I’ve annoyed you. I don’t think we should get together tonight. We will either choose to try and this will sort itself out naturally but I don’t want to force anything today.”

I’m pissed. “Thanks for fucking with me two nights in a row,” I tap back, furious. I feel like a fool for suggesting we hang out, because he’s right: We shouldn’t see each other tonight. I don’t want to see him. I want to yell at him. He’s ruined everything! If he had just been honest with me.

“How did I fuck with you two nights in a row?,” he texts back. I decide not to respond. I am deflated. Now there is nothing to look forward to, not even an argument.

10:00 a.m. The feeling that is growing inside me is one I know all too well: My ex and I used to get in exhausting arguments where one person (me) would say something and the other person (him) would shoot back something completely unrelated, to which I would be tricked into responding until the yarns of our emotions were hopelessly tangled into hard little balls of resentment. I’m not wasting my time again. Better to cut ties now before four years slip by. Fortunately, I have lots of work meetings to keep me busy today, and I quickly arranged a date with B tonight. He’s making pierogis for me and his roommates.

6:00 p.m. I arrive at B’s house stoned out of my mind and carrying some cookies. It turns out he won’t actually be making the pierogis — his dad sent them to him, frozen, from some Ukrainian grocery in Minnesota.

7:00 p.m. Dinner was actually pretty lovely, even though I almost nodded off at the table as B droned on about his upcoming vacation to San Francisco, encouraged by his roommate Katie (they are pretty close, but I’m not jealous yet). Meanwhile Katie’s boyfriend Jack subtly expressed his annoyance by stretching, harumphing, and clanking his big new vape pen around.

9:00 p.m. After dinner, we had sex. B is certainly the most theatrical lover I’ve ever had, twitching about and moaning and calling my name and saying I have a “powerful pussy.” He coated me in some sort of lube and put me on top of him, so my back was on his belly and his hands were slipping up and down my boobs. I felt like a fish in his bed.

After B came (I came earlier, after a little tongue and finger action) I nuzzled my face into his neck (he smells delicious) and he gave me a squeeze. All of a sudden I imagined that his arms were my ex’s. And then his arms turned into H’s and I squeezed out some tears. I hope he couldn’t tell, but don’t plenty of women cry after sex?


1:00 p.m. B gave me a pierogi to take home, and I’m enjoying it for lunch today while wondering if he’s going down to San Francisco to see a girl. But that is the smoldering anxiety in me that I must tamp down with healthy, intentional decisions, not haphazard leaps into emotional puzzles I don’t actually need, or really care, to solve.

4:00 p.m. A fair amount of my work involves coordination, not something I’m terribly good at. Details make me anxious and I’m always forgetting essential ones. Once I heard that perfectionism isn’t always doing things perfectly. Sometimes it’s being paralyzed by all there is to do and knowing you won’t be able to do it perfectly, so you don’t do anything at all. I think this might be a way for slackers to pass themselves off as perfectionists, but I’ve been looking at this spreadsheet for an hour, immobilized by doubt about how to arrange the information. I decide to answer emails instead. That’s how days pass without me actually getting anything done …


9:00 p.m. I was supposed to have a date with L tonight, but I flaked on him. He’s an amazing graphic designer, probably one of the most interesting people I’ve ever dated. We haven’t kissed or had sex yet, and part of the reason I flaked is because this is the date where we probably would. But I’m feeling sexed out and a little emotional. I spend the night watching Desperate Housewives, eating shortbread, and drinking cocoa and peppermint schnapps. I’m dog-sitting for a friend, and the dog sleeps in bed with me, curled up under the covers right next to my belly. He’s sweeter than any man I’ve ever known and brings me far more joy. My mom and dad keep advising me against getting a dog. They’re probably right, but it’s not like I’m doing anything that would prevent me from being a good dog mom. I could afford to put a little more energy into myself and a little less energy into men I’m bound to know for only a short amount of time.


11:00 a.m. I wake hard and stumble outside to walk the dog. Now that I’m 25, eating and drinking right before bed actually makes a difference in the way I feel. H laughed when I told him that.

5:00 p.m. My friend invites me out to happy hour drinks. She started off as my co-worker, but now we’re basically BFFs. I always feel better after hanging out with her — the mark of a true friend. She listens to me bemoan my current romantic situation and gets tipsy after half a beer. We have two rounds and hug good-bye outside the bar.


10:00 a.m. C asks me to the movies tonight. Monday night movie? I’m down, especially because I know he’ll pay for it, as well as some popcorn if I express even the slightest interest. Plus, going to the movies means we won’t have to talk. I feel kind of bad for C. He’s 30 years old and recently divorced. We met on Tinder, of course, and he told me he doesn’t want to be on it for too long, which sounds to me like he wants to get into a relationship soon. That is exactly what I don’t want. Except maybe with H, who has made that an impossibility.

5:00 p.m. Work is something of a drag today — a lot of meetings that don’t really pertain to me. By the time it’s over all I want to do is lie down, but I go home to get ready for my date.

10:00 p.m. We make out in C’s car after the movie. I kiss his neck softly and joke that I don’t want to leave a hickey, since that would be unprofessional. He’s a real-estate agent and has a house showing tomorrow. “Ah, I love you,” he says in response. I pretend I don’t hear that. He pretends he didn’t say that.


9:00 a.m. I know that C didn’t mean to say he loves me, but the thought makes me so damn sad I think I’m going to have to stop seeing him. I’m a few years younger, but I can still relate to his need for connection. But I’ve decided to spread that over as many men as possible, so none of them have to bear the brunt of all that need. At least until I figure out what I’m really looking for in a guy …

6:00 p.m. I don’t think that H is going to text me again, even though he’s active on Match just about every time I open the app. Was he just after the chase? If he had just been honest with me, or at least not lied so obviously, I could accept it. I’m seeing other people, he can too. But I spent four years with a liar — I’m not going to waste any more time than that. My friend’s back in town, so the dog is gone. Climbing the steps to my apartment and knowing I won’t see him zoom around the apartment in celebration of my return, I feel sad … but not hopeless.

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The Woman Afraid of Leaving Hickeys on Her Divorced Date