Regretting That We Ever Met



What’s your gender? Woman
How old are you? 29
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: Post-graduate degree (currently pursuing)
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

Regretting That We Ever Met

How long ago did this hookup happen? 2 months ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He was a few years older than me. We met on Okcupid. He was intelligent, funny, interesting, and slightly attractive. Not my type, but I was lonely. He had red hair, pale skin and expressive eyes. We met on OKcupid and went on a date. We had coffee first, then he asked me to have brunch with him. Then we went to a park. It was nice, I had a good time. But I wasn’t sure of his interest in me. I had just moved to this new city, and was feeling nervous after a series of terrible dates and no sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After the date, we were texting and decided that he would come over to my place the next weekend. I was a little hesitant, but thought we could just watch TV and eat, maybe cuddle and make out. I hadn’t had sex in six months, and I wasn’t planning to with him. I just missed being in someone’s arms.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We watched a couple hours of a show and ate pizza on my couch. Then all of a sudden he asked to kiss me. I was so nervous. I hesitated, then we kissed. I held his hand and I felt my guard coming down. He stood up and asked if we could go to my room. I didn’t want to, but I said okay. We got on the bed and started kissing, when he grabbed my hips and started touching me everywhere. I was taken aback and said, I thought we were just going to cuddle. he said, that usually happens after sex. He laid down, I was very nervous and laid down next to him. He started talking really dirty, then he fingered me and asked if he could take off his pants. That felt really good. He tried to go down on me but I stopped him. He started masturbating, then he came on me. After that, we talked a bit and cuddled. Then I told him, I wanted to have sex. I felt, I want to please him and I wanted to not feel alone. His penis was wide and sort of uncomfortable. He seemed a little inexperienced. We did it from the side. He couldn’t come inside me, he said due to issues from a past relationship. He came on my stomach again. We cuddle and talked then he left. We made plans to meet again, after he got back in town.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Afterwards, he was traveling a lot and very busy. Sort of ignoring me. I texted him to tell him I felt disappointed and saddened by his lack of attention, to which he replied negatively and told me he didn’t think we were a good fit. It hurt very much. I regret having sex with him and wish that we never met.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, I was feeling lonely, Everyone else was/is doing it

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I said yes, but only to please him.

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I told a family member and a couple friends. They tried to encourage me that things would get better.

How would you best summarize people’s reactions about this hookup? Relatively negative

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Very much

Why do you regret this hookup? Because I did it to please him, not myself. And because he didn’t really pay attention to my emotions afterward.

What was the BEST thing about this hookup? Talking to him and sharing our feelings before and after.

What was the WORST thing about this hookup? That I had so many emotions afterward, and that he didn’t care enough to be patient with me.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I still feel the same as always, that I don’t care to date or have sex too often and protect my fragile emotions.

All things considered, how POSITIVE was this experience? Not at all positive

All things considered, how NEGATIVE was this experience? Fairly negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I think it is fine for some people, and I wish I could explore my own sexuality more. But I need my emotions addressed afterward.

What do you think about the Casual Sex Project? It’s interesting.

You have a hookup story to share? Submit it here!