Ask Dave-Should We Date Or Be Friends?

A woman wonders if her best pal should become her lover. How to sort through this situation?

By Dave Singleton

ear Dave,
I’m a woman in my mid-twenties. I recently met a woman my age and we’ve become very close. Honestly, she’s the friend I always wished I’d had, the stereotypical best
I am open to dating a woman if she’s the right person for me.
friend that hardly anyone really has.

Here’s the thing. When I met her, we were both pretty certain that we were straight. She had, and still has, a boyfriend. I’ve thought about my life pretty hard and, though I still like guys, I am open to dating a woman if she’s the right person for me. A few weeks ago, my new friend told me that she was in love with me. She made it clear that it wasn’t platonic. If she were single, I’d just say we should try it out.

But she still has the boyfriend. Whatever she feels for me aside, I think she’s looking for an out to her four-year relationship. I’ve gone from wanting to encourage her to feeling used to fear of seeing her altogether, because I’m afraid to think of this ending badly. It’s very important to me to have her as a friend down the road. I’m a pretty quirky person and to find someone else who fits me so well is rare. What should I do?

Dear Floored,
I’d say that you are putting the cart before the horse to consider a relationship with her right now. But really, the cart and horse are so far apart that I am not sure I can even make that statement.

It sounds like you both really care for each other, which is wonderful. So I’d focus on your friendship as you consider dating. As you note, a close friend is a rare gift.

Should you date her? I think you are wise to be apprehensive about the possibility. She is unhappy in a relationship and considering a breakup at the same time that you both are entertaining the idea of a same-sex relationship. I am not sure which of these two flags is redder:

The breakup.
Any breakup is bound to be traumatic, and the end of a four-year relationship will cut deep. Even if she’s in love and wants to start a new relationship with you now, she’s not taking into account time for healing, getting over guilt, or even a courtship period. Regardless of sexual orientation, breakups create a hurricane of feelings. Your new relationship would be directly in the eye of that hurricane.

The same-sex relationship.
Even if you both have felt attraction to women before, it sounds like you’d be acting on it for the first time (at least in terms of a relationship). As you say, “When I met her, we were both pretty certain we were straight,” and that was just a short time ago. In other words, you both sound like newbies. In addition to dating issues that are common to all, such as sexual compatibility and handling increased intimacy, you’ll likely face a shifting uncertainty over your sexual identity in general.

Proceed with caution.
I think the best thing to do is slow down the potential timeline and proceed with caution. Don’t get romantically/physically involved too soon. That might work for some
Tell her in as easygoing a manner as you can.
people in some situations, but it doesn’t sound like it will work for you. You have very strong feelings for this woman and you need to respect them. Don’t further complicate your life until you feel more comfortable about where this could lead.

Since you’re facing a myriad of conflicting feelings, from desire to confusion, take time to sort through them. Do you return her love? If she were single, would you want a romantic relationship with her? If the answers are yes, then the next steps are:

Express yourself.
Find a time when the two of you are relaxed and spending time together (don't do this over the phone or in a letter), and tell her that you’d like to consider a relationship with her, but only when she’s completely disentangled from her current relationship and has had some time to regroup. Tell her in as easygoing a manner as you can. There are big issues to discuss, but remember that it’s time for initial talks, not an ultimatum.

Put your concerns on the table.
Share with her your fear that she might have latched onto a romance with you as a lifeline to pull her from a relationship that is drowning. You don’t want to be just a means to an end. Find out if she wants to pursue a healthy, real relationship with you... or is she just looking for an out from a relationship that’s no longer working.

Talk about the future.
Is she planning to end her current relationship and, if so, when? If she does, would you agree to slowly start seeing each other? Do you both feel the same way about preserving a friendship even if a romance doesn’t work out? It’s not easy to ask such blunt questions, but you could save yourself a lot of heartache down the road by being clearer upfront.

If you talk and decide, for whatever reason, not to pursue a romance, then focus on how you can create a healthy friendship. It might take some time apart and/or a lot of talking things out to reestablish a healthy, balanced friendship with no hidden agenda on either side.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Visit Dave’s website and send your dating questions and comments to him at
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