‘I Want To Be With a Woman, but My Inexperience Makes Me Feel Really Insecure’

Q:

I’m going to try to write something that makes sense, though it’s hard because I’m a mess right now.

Here is the thing, I’m a cis woman in her early 30s who has always labeled herself as bi. It’s something I have always said without giving it much tought. I have said it, but I haven’t really explored it in any way.

When I was in highschool and college I didn’t have any real crush for anyone (or at least I’m sure I didn’t have it for any man), and I only dated for a while one person (a man), though I couldn’t make myself do anything physical with him appart from a peak on the lips now and then.

Time passed by and I spent my 20s focused in myself (mainly self-esteem and work), I had an objective I wanted to reach. After much work I finally got to the point where I wanted to get, but, on the other hand, I avoided dating or getting physical with anyone. I really found no man I was interested in, and the girls I had crushes on were heterosexual.

The thing is that I now find myself in a point where I want to finally be with someone and I just want to meet girls, so I am questioning my label as bi, which, at the same time, makes me feel guilty because of internalised homophobia (yeah, such a great thing). I opened up a dating app profile because I don’t really know how else to meet women. However, everytime someone asks me about my dating history, I feel sick. On the one hand I want them to know about it (just because it would explain a lot if anything physical ever happens) but, on the other, I fear being “made fun of” or “rejected” in a way. I’m not naive, I know a lot of stuff, I have simply not really done anything with anyone or by myself (something I’m working on). I want to be with a woman, but my inexperience makes me feel really insecure and I don’t really dare to take the lead.

I know my story has brought up a lot of different issues, but I guess I ultimately want to ask whether my situation is that unusual and if you have any advice to finally dare to be with a woman and stop feeling like I am doing a bad thing for not “trying hard enough” to be with a cis man.

A:

Hello! Everything you’re feeling is incredibly common — from the internalized homophobia to the label questioning to the anxieties about your relative inexperience. So to start, no, I don’t think your situation is unusual!

If you want to meet girls, then I think it’s time to meet girls! If it helps, I think you can press pause on figuring out exactly how you want to label yourself. There’s no reason that needs to be perfectly figured out now, and sometimes the experiences we gather from dating around actually help us explore and settle into ourselves. If thinking about labels is kicking up too many sticky feelings, then let’s step away from that for now. You’re putting so much pressure on yourself!

We get questions from people who fear reactions to their lack of sexual history and experience all the time. But here’s the thing: In all my years of being gay on this planet, I’ve never heard of someone being rejected or made fun of for their lack of sexual experience. I think especially when it comes to queer dating, it’s quite common to encounter people with short or nonexistent sex and dating histories because a lot of us spend chunks of time in the closet or otherwise have a lot of shame around sex. I’ve been people’s first queer sex experience, and for me that’s more exciting than it is anything else.

If you don’t want to take the lead, you don’t have to. It’s best to be clear about where you’re at upfront, because it’ll make it easier to find people who are a good match for you and who will be more than happy to take the lead. I think your instinct to let them know is right, and even though I understand your fears, I think they’re largely unfounded. And for what it’s worth, just because people do have experience being physically intimate doesn’t automatically make them experts, especially because sex can vary from partner to partner.

The only way to gain experience is to put yourself out there and give the dating app a real go. I think you’re being held back by questions of identity and some insecurity about your past, but I don’t think we have to figure it all out before we jump into dating. You’re going to learn so much about yourself from the actual process of dating around, and I’m excited for you to get out there and meet some women! There’s no better time than New Year’s to make a new commitment to yourself and really put yourself out there. I’m wishing you so much luck!


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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 951 articles for us.

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