Hookup Help: Friends-with-Benefits Advice

Q: Dear Tia. Three months ago I met a woman with whom I began a no-strings-attached sexual arrangement. The whole purpose of our meeting was to help her overcome some issues she had with letting go and feeling comfortable in bed. I’m a few years older than she is and I’ve had lots of experience, so I offered to be her “practice partner”. For the first couple of months things were going great. We were meeting once a week at my place and having an amazing time. The sex was way better than I think either of us expected and there was an undeniable spark between us.

The trouble is I suspect she’s developed deeper feelings for me. We both got into it knowing that I would be leaving the country soon and agreed to keep things casual. What can I do to let her down gently, now that my move is upon us? Part of me just wants to bolt, but I know that’s the wrong thing to do. I feel so terrible when I think of hurting her. Thanks. – David

A: Dear David. You sound like a very caring and sensitive man.  It’s no surprise your partner felt comfortable enough to open herself up to you. It can be hard sometimes to keep the emotions out of casual sex, especially when there’s a real connection. That said, you both entered into this knowing what the boundaries were and as a grown woman, she is responsible for her own feelings. I completely agree with you that running away is the wrong thing to do, but so is beating yourself up for choosing to follow through with your plans.

I would sit down and talk with her, being completely honest about how the situation makes you feel. Give her a chance to really understand your feelings first, then give her an opportunity to express hers. You speaking first will give her the option of choosing how much she wishes to divulge about her hopes for the two of you. She may wish to protect herself and not express anything at all, but that’s her call. At least you’ve given her an indication of where you’re at.

She might end up admitting that she wishes the two of you could be a couple. It’s okay to hear what she has to say without feeling guilty. I know that might seem harsh, but you were upfront with her about your plans from the start and her feelings are hers to own.

Something else to keep in mind is that depending on how deeply you feel for one another, there might actually be an opportunity to start a relationship if either of you are willing to compromise. Before you speak with her, take time to consider what you really want. It sounds like you are a bit conflicted and that there might be something deeper to your concern for her, if you choose to accept it.

Rules for Friends with Benefits

Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex… we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter. -xo Holly and Tia

Ready to Find Local Hookups?

Explore the Best Hookup Sites for Getting Laid in 2022.

Find Hookups Now

Tell us what you think

Notify of
Inline Feedbacks
View all comments