I am a cigender woman in my forties. After separating from my former husband of fifteen years, I am starting to get back in touch with my sexuality, and in this process it has become apparent that I may be bisexual. I have developed a crush on a lady friend of mine of many years, who is a total babe. Given my inexperience with women, I am at a loss as to how to bring up to her I may be interested in her without potentially ruining the friendship forever.

Newly LGBeeeeeTQ

Dear LGBeeeeeTQ,

I imagine that this is a very emotionally charged time for you. The end of long-term relationships can really reveal a lot of new things about ourselves, sort of like turning the soil in a field that has lain fallow for a few seasons. Everything feels new, even ourselves. It’s not uncommon to discover new truths in the midst of these transitions, learning unexpected truths that bring us closer to our authentic selves.

I believe the best first step is to reflect seriously on your feelings before saying anything. Not just the feelings about your friend, but also about your sexuality. Exploring fantasies in real life can be awesome—sometimes it can even be life changing. But it’s very important to remember that your friend is a whole human with her own complex set of feelings. Humans are, well, human. Most of us carry around a lot of cultural baggage, and that baggage can be full of shame, guilt, previous experiences (good and bad), learned coping mechanisms, denial, and fear. Approaching any new romantic or sexual relationship can pop the lock on that baggage. This can be even more pronounced with LGBTQ+ relationships, which can still be laden with stigma even in these relatively accepting times.

Next, think about what you actually want from this friend in your ultimate dream scenario. Are you looking for a hook-up? A relationship? A friends-with-benefits situation? Is your main motivation is to have new sexual experiences (super valid and fun!)? Or are you equally (or more) interested in having an ongoing relationship with her (think girlfriends instead of gal-pals)? Whatever you figure out, be prepared to discuss that honestly with your friend as well?

If you decide to move forward after all of the reflecting, thinking and considering, I recommend the old “prepare for the worst, hope for the best” strategy, which is sort of what dating is like all the way around.

A common way to ease into these conversations is to share you’re discovering your burgeoning bisexuality and see how she responds. You may get lucky and she’ll tell you that she’s also bisexual or exploring her sexual orientation. That might just give you the opening you’re looking for immediately. Or, she could respond by declaring that she really loves men and only men (this happens more often than you might think!), which would also be fortunate for you. If that’s her response, you’ll know that moving forward with your declaration would be very risky for your friendship indeed.

When you want to move the conversation from “I think I might be bisexual” to “I think you’re a total babe and I’d like to date you,” consider divulging your feelings for her by text or email to give her the space to process without the pressure of an immediate answer. Be honest and clear in your communication, but also kind and respectful. Tell her what you want (or think you want) as a next step. For instance, do you want to go out for drinks and talk more? Or maybe you’d like to try sharing a kiss the next time you hang out? What about an at-home evening of rom coms and cuddling? Activities like make your intentions very clear. At the same time they are generally non-threatening, giving her the opportunity to really think about what it would be like to start this adventure with you.

It’s also a good idea to tell her to take her time before responding so she can give you a thoughtful and honest reply. Be clear that you value the friendship even if she’s not interested in you romantically or sexually. If she says ‘no thank you’ to changing the dynamic of your friendship, respect whatever boundaries she sets as you move forward platonically. If that happens, you can process your feelings about this rejection with other supportive friends, not with her. That would be your work to do, and she shouldn’t be expected to help you through that.

If she responds enthusiastically, the two of you can collaborate about what happens next! And that’s when the real fun begins.

Curious about cunnilingus? Anxious about anal? Do you have questions about queefs or problems with your prostate? Lucky Tomaszek is the education coordinator at The Tool Shed: An Erotic Boutique, Milwaukee’s only mission-driven, education-focused sex toy store. Send her an email at [email protected] and she’ll get back to you with an answer.

About The Author

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Lucky Tomaszek, LM, CPM, is the education coordinator at The Tool Shed: An Erotic Boutique, Milwaukee's only mission-driven, education-focused sex toy store. Most mornings you can find her balancing her cat and her keyboard in her lap, working to make the world a smarter, safer place for people of all genders and orientations.