Q:

I am a 50 year old woman who has exclusively dated men for the last 30 years. I dated a girl in highschool but it was a different (and very homophobic) time. The relationship ended very publicly and humilatingly and ultimately tragically for both of us. I have had sex with a few women since but publicly I only have only had relationships with men. Mostly due to lingering fear and shame.

Now that I’m older and have somewhat dealt with my youthful trauma, I would like to begin dating women again. Is it too late? Is having been primarily with men for 30 years a dating deal breaker for a lot of lesbians? How do I approach letting someone know I am a novice at gay sex when even though I’m older? Do I need to fess up to my heart breaking highschool experience or explain my 30 year break from women to each new potential partner?

Thanks,
To Shy to Have Asked Sooner

P.S. If anyone wants further clarification, in highschool I had a girlfriend (we were not out to our families). Her parents caught us having sex one morning and forced me to walk home only partially clothed in winter (through our small semi-rural town). They then put her in a mental hospital under false pretenses and sent her away to finish high school. She died a few years after high school so we never got to resolve what had happened between us. I have always felt deep shame that her life was horribly altered and made very difficult by her parents finding out about us. Her mother made a point not to invite me to her funeral. My friend had worked so hard to repair her relationship with her family that I didn’t even want to ask to attend.

A:

First of all, I want to thank you for sharing your story with me. You didn’t have to include the postscript at the end of your letter in order for me to answer this question of yours meaningfully, and I know that took a lot of vulnerability, so please know I’m so appreciative. It is a very sad story, but I am also very moved to hear it and to hear that you have “somewhat dealt” with your youthful trauma.

So now let me get to the point: It is never too late to start dating women. Your 30-year break from dating women makes a tremendous amount of sense. And hey, even without the sad and traumatizing backstory, it actually doesn’t matter! Someone can spend thirty years of their life dating men only to realize they actually want to date women in their fifties for any reason at all. The fact that you have worked through your fear and shame enough to even just want to start dating women is HUGE! Congratulations, that’s amazing!

Now, don’t be the one to hold yourself back from actually pursuing that want. If having been with men for thirty years is a dealbreaker for someone, it doesn’t mean there’s anything wrong with you, it just means that person isn’t a good fit for you (and, if I may editorialize a bit, means that person is a bit silly, too). In any case, I feel confident it is NOT a dealbreaker for “a lot of lesbians,” as it wouldn’t be a dealbreaker for any of the lesbians I personally know — and I know a LOT of lesbians! It is practically my job to be a lesbian!

Rest assured: You are far from the first person to worry about relative lack of queer sexual experience. You’re not alone! So lucky for you, we have a whole archive of advice pieces about how to navigate such situations, including:

• ‘I Want To Be With a Woman, but My Inexperience Makes Me Feel Really Insecure’
• ‘I Just Realized I’m Bi and Am Extremely Anxious’
• You Need Help: Telling Someone How To Sex You Up
• You Need Help: Do I Disclose That I Haven’t Had Sex In a While?
• ‘I’m a Sexually Inexperienced Stud Afraid of Doing It Wrong’
• You Need Help: It’s Okay If You Haven’t Had Sex Yet

A lot of the pieces above convey similar sentiments: that it’s normal to feel stress about inexperience but also that it won’t be a turn off for most compassionate people. And at the end of the day, what works sexually for one partner does not necessarily work for another partner because of how different everyone’s bodies, brains, desires, and histories are. So “experience” doesn’t automatically make someone an expert in how to get a new lover off.

I feel pretty confident that if you do disclose your inexperience, no one will hold your age against you. Coming out in your fifties is not all that strange these days!

I do not think you have to immediately disclose your backstory with your high school girlfriend if you do not want to. It’s a very personal story, one you should only share when you genuinely want to. There’s no reason you’re required to, especially when first starting to get to know someone. If you mention not having dated women for thirty years and a well meaning date is curious as to why, you can leave it vague by saying something like “I had a lot of shame and fear around queerness.” That’s totally alright!

As you get to know someone on a deeper level, talking about your story will probably naturally happen on your own terms and, ideally, with a person you feel safe with. It’s not a story that’s going to send someone running.

I’m sorry about what happened to you in your youth, and I am sure that is grief you carry every day. You can still date and meet women through it all, and I hope you will. It’s clear you’ve already done a lot of work to heal, and I think you can consider dating and putting yourself out there as a continuation of that healing process, not something that is at odds with it.

Also, find community if you haven’t already! Making queer friends of all ages is a great way to help with some of the lingering feelings you’re experiencing around fear, shame, and insecurity. Making queer friends is as essential to this journey as beginning to date, if not more so. Sending you love!

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