Rebound sex/losing virginity casually?

[altrockhudson]

Hi everyone, this is my first post on Scarleteen! I'd appreciate some non-judgemental advice, so I thought I'd try here.
I have a really close friend who I am in love with. This has been going on off-and-on for years- I was in love with her a few years ago, then we drifted because of COVID and a few fallings-out, and now we're very close again and I feel exactly like I did before. The feelings are somewhat mutual- she has a crush on me and could hypothetically see something happening between us in the future, but she has a boyfriend who she's pretty serious about. I think they're going to be together for quite a long time, and I want to explore my sexuality with other people, but I'm really hung up on her. I am a virgin, and while I know that virginity is a construct, I always wanted my first time to be with someone I loved, and for it to be romantic. I don't know if/when I'll get over my friend, and I don't think I'm in a place to fall in love with anyone else. I don't meet many new people anyway, so I don't know when I'd even meet another potential partner.
I know at least one person who I think I could hit up for casual sex- she's a friend and a really lovely person, but I don't think I feel romantic feelings for her beyond a baby crush. I am debating whether to have sex with her- I want to experience things, and I don't want to wait for someone that I might never date, but I also don't want to regret my one shot at having sex for the first time. I feel like sex won't be as special afterwards.
I feel like I'm rambling, but TL;DR- should I wait to lose my virginity with my currently unavailable friend, or should I do it more casually with someone else?
Thanks!

[Mo]

Hi there altrockhudson, and welcome in!

As a very general statement, I think it's good to make plans for the future, when it comes to relationships, based on whatever people are telling us now, in the moment. It sounds like your friend is expressing some level of attraction to you, but that she's currently with a serious partner (who I assume she's monogamous with, based on what you've written here), so sex or a relationship aren't currently something she's interested in pursuing with you. It might be something she's interested in sometime in the future, but I think making plans based on that possibility isn't going to be the best or healthiest option for you, regardless of what happens between you in the future.

When it comes to the friend you're considering casual sex with, it isn't clear from what you've said here whether you've ever talked to her about this possibility. Is this something that's come up between you before?

[altrockhudson]

Hi there altrockhudson, and welcome in!

As a very general statement, I think it's good to make plans for the future, when it comes to relationships, based on whatever people are telling us now, in the moment. It sounds like your friend is expressing some level of attraction to you, but that she's currently with a serious partner (who I assume she's monogamous with, based on what you've written here), so sex or a relationship aren't currently something she's interested in pursuing with you. It might be something she's interested in sometime in the future, but I think making plans based on that possibility isn't going to be the best or healthiest option for you, regardless of what happens between you in the future.

When it comes to the friend you're considering casual sex with, it isn't clear from what you've said here whether you've ever talked to her about this possibility. Is this something that's come up between you before?

Hi, thanks for replying! I think you gave some good advice. I have had some conversations with the friend I'm considering casual sex with. We had a weird romantic fling a couple of years ago that ended because she was unwell at the time, but she is now better. We have also both been very open with each other about looking for casual sex and potentially sleeping with friends. I don't want to assume her answer, but the subtext I get from her is that she would probably say yes if I asked, although I can't read her mind and it is obviously well within her right to say no.

[Mo]

That's helpful to know, thanks! It might be helpful to read through this article about casual sex when you're making decisions about how to proceed here. The big piece of advice I have about casual sex with a friend is that it's good to be really clear about what you're each looking for from the experience.