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Ask Dave-Friend Or Lesbian Lover?


One woman wonders whether to let her best pal know about her romantic feelings.

By Dave Singleton

ear Dave,
I’m in love with one of my best friends. We are both in our early twenties and I have been in love with her since we met almost a year ago. We’ve been amazing friends since the first day we met and I can’t imagine my life without her. But I have a lot
You don’t have to set this up as an “either-or” decision for your friend.
at risk. I have yet to tell her my feelings, because she remains in an on again/off again relationship that seems to be driving her crazy.

I have tried for the last several months to get over her, with several sleepless nights, but it is just impossible. I want to tell her how I feel, but I am scared that, if I do, not only will I be rejected, but also I’ll lose my best friend. Should I just keep my feelings to myself and take the pain or risk it all?
– Is It Worth the Risk?

Dear Risk,
Whoever came up with the well-intended phrase, “nothing ventured, nothing gained” probably didn’t experience sleepless nights worrying about how to profess great love to a friend.

But there’s always something to be learned by taking a chance, and more of us regret the paths not taken more than those we walk, no matter how they turn out. So no, I don’t think you need to keep your feelings to yourself and suffer in silence.

But take some time to say what you want to say in a smart way. You don’t have to set this up as an “either-or” decision for your friend. You aren’t trying to give her an ultimatum, are you? You are just being honest. Sometimes, how you say something is more important than what you say. It seems to me that the best step you can take is to carefully think through the possible outcomes and get as comfortable as possible with each.

It’s important that you are comfortable with whatever outcome arises. It’s a much less risky proposition if you’re able to give her the space to feel whatever she feels, without worrying about crushing you or facing an ultimatum.

So keep in mind that nothing is impossible, but remember that the truth about unrequited love is that it usually meets with one of three fates:
  • Your love is finally reciprocated and a new relationship morphs from the old.
  • Your feelings subside for whatever reason, and you move on in ways you can’t even imagine now.
  • You discover that your feelings are not returned and then, with time, channel your love into someone new who, hopefully, will return it.

If considering these three scenarios feels daunting, talk them over with a close, trusted friend or counselor. And while you are at it, take
There’s a slight chance she might choose to end the friendship.
as objective a look as possible at her on again/off again relationship. What can you glean about how she acts with a girlfriend? What does she seem to want? What is she willing to give and not give? Why would she stay in a marginal relationship for such a long time? Take your rose-colored glasses off long enough to see that just because you love her doesn’t mean that there’s a healthy relationship waiting for you. She has to love you, and be compatible and available, in order for any potential relationship to stand a chance.

Once you’ve thought things through and are comfortable with each possibility, find a neutral, relaxed setting and tell your friend how you feel.

When you tell her, be sure that you:
  • Let go of your hidden agenda. Right now, you aren’t building your friendship on honest, solid ground. Be conscious in your approach going forward so that you’re positioned to keep a friend (if that’s all it is) or respectfully seek more.
  • Emphasize that you value her friendship. Let her know that you hesitated to tell her the truth and risk losing what you have together. Your honesty reflects your respect for the friendship.
  • Accept her responses. While it’s good to be honest, it’s also important to respect her feelings about dating you, her current on again/off again girlfriend, or, frankly, no one at all. Don’t try to change her. Assume that she means what she says.
What could happen once you spill the secret?
You could become closer. Sometimes, honesty propels the relationship forward, with or without a romance. Your honesty may inspire her to be more truthful with you about who she is and what she wants, which, admittedly, seems vague right now. If she wants to date you, you’ll have quite a transition to make, since she’ll need to turn her on again/off again relationship “off” for good. If not, you’ll set the stage for a more honest dynamic.

Or, there could be a temporary awkwardness. Romance or not, you may experience fits and starts of communication as both of you adjust to truth out in the open. For example, you might second-guess each other’s motives for interchanges or delayed return phone calls and emails. If she just wants to be friends, you may need distance (even if temporary) in order to heal and move on. In time, you can re-establish your friendship based on reality.

The unlikely worst-case scenario is that your friendship ends. There’s a slight chance she might choose to end the friendship. Or, you might discover that you can’t be “just friends,” that you need to separate in order to regain your emotional balance, and pursue a romantic relationship who’ll return your feelings.

Bottom line: Tell your friend the truth in a respectful way, and let the chips fall where they may. Yes, it’s a risk. If the truth is ventured, integrity is gained, no matter her response. And that’s worth a lot.


Dave Singleton, an award-winning writer and columnist for Match.com 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 davesingleton.writer@gmail.com.
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