Follow through
March 15, 2012 8:35 AM   Subscribe

How do I sleep with a woman? If I am a late 20's woman who has never done so before.

So....... I think I might be interested in women, but I'm not really sure. I'm not looking for a long-term relationship or anything but I'm also not really into the club scene. Craigslist is not appealing on many levels. There must be other websites or something? I'm an introvert, quiet, not-great-at-dating-or-meeting-people blahblahblah, type etc.

Other relevant details: Currently in Toronto. Friends with many gay/queer people and am totally comfortable with people *thinking* I am into women (although they generally do not)... my problem is, I guess, follow through.
posted by anonymous to Human Relations (11 answers total) 9 users marked this as a favorite
OKCupid -> specify: looking for Casual sex/"activity partners"-> Women who are attracted women only -> Not looking to be part of your 3-some TYVM
posted by MangyCarface at 8:40 AM on March 15, 2012 [4 favorites]

Okcupid has tons of bi and gay women, and is free, and is very fun and low pressure.
posted by empath at 8:41 AM on March 15, 2012

(also, the other thing about Okcupid is that it's not necessarily a 'hook-up' site if you're worried about it being skeevy. It's totally fine to just go on their looking for friends, and lots of people do.)
posted by empath at 8:43 AM on March 15, 2012

Please, please be up front in your profile or on the first date that you are bi-curious but unsure if you are definitely into women. There are plenty of women who will still be interested in you, especially for a casual thing. However, some women will not be, because they don't want to get involved with someone who might turn out to not be into women at all.
posted by insectosaurus at 8:49 AM on March 15, 2012 [9 favorites]

OKCupid, be upfront that you're bi-curious and looking for a fling, yes.

If you want to research, The Whole Lesbian Sex Guide is the lesbian equivalent of The Joy of Sex.
posted by Sidhedevil at 8:54 AM on March 15, 2012 [2 favorites]

Friends with many gay/queer people and am totally comfortable with people *thinking* I am into women

Hang out with your many gay/queer friends and let them know you're looking. I'm straight but experimented with this years ago and found going to my friends to be the fast-track.
posted by sweetkid at 9:02 AM on March 15, 2012 [1 favorite]

OK Cupid is what many people use for finding flings, casual relationships, one-night-stands, etc. However, while there is nothing wrong with casual sex or online dating, not everyone can just jump right into that kind of thing. I was you about 10 years ago, and I had real trouble with this. Sure, in theory, I wanted to meet a nice woman and try dating her, but in reality, not just any woman would do. It was more than a little terrifying.

I would suggest looking around your local LGBT community to find a nice way to meet some new women instead. Look for a group that caters to young women, because those groups will be more likely to involve a lot of women like you who are bisexual. Book club, discussion groups, outdoor activity club... Meetup would be great for this, actually. Go to an event or two like that. See if you click with anyone, then make a move if you can work up the courage to do it.

At least try meeting people IRL as you're doing the OK Cupid thing- it will feel less desperate to you and you'll come off better on the dates.

Do be honest on a first date with anyone about where you are with your process, that you're new to this. Don't suggest more commitment than you can give, and if this means that they aren't willing to go further with you, then be ready to accept that answer.
posted by aabbbiee at 9:24 AM on March 15, 2012

A friend of mine recently had similar feelings and she met her first girlfriend through friends. Since they've broken up, she's now on OKC.
posted by anotheraccount at 9:29 AM on March 15, 2012

Please, please be up front in your profile or on the first date that you are bi-curious but unsure if you are definitely into women

However, for OKCupid specifically if you are not looking to date guys, I suggest that you do not put bisexual as your orientation selection in your profile settings, just make it clear in the text of your profile. The reason for this is that by default, when a straight guy searches OKCupid, it shows any woman's profile who is listed as straight or bi. That means even if you spell it out in your profile in great detail that you have no interest in being contacted by dudes, a lot of clueless guys will send you messages anyway, and since straight guys send out tons of messages on the site your inbox will be full of them. Some people will be miffed that you set your orientation as only being interested in women when you actually are also attracted to men, but from a sanity standpoint being excluded from the search results of guys who you aren't interested in is the best choice.
posted by burnmp3s at 9:48 AM on March 15, 2012 [5 favorites]

Agree with using OkC, putting only interested in women, and being upfront that you are curious- but could be down with just being friends with people. You could at the very least meet some more cool queer people who are looking and who could introduce you to their cool queer friends who are looking.

Second best recommendation- look on, or look up queer groups or HRC, for book or discussion or volunteering groups around queer or feminist issues.
posted by forkisbetter at 10:43 AM on March 15, 2012

Another point about OKCupid: as a bisexual woman, you'll probably get emails from poly women who are already in a relationship with a man. The women were generally looking to have a side relationship with a woman, often because they were bi-curious. They weren't (necessarily) looking for a threesome or a third in the relationship. They just wanted to explore this, and their boyfriend/husband was fine with it.
I'm not into polyamory and this turned me off. You might be fine with this and it might be exactly what you are looking for. Either way, it may come up.
posted by aabbbiee at 11:39 AM on March 15, 2012 [1 favorite]

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