“Should I Tell My Longtime Friend I Have Feelings for Her?”

I’ve been reading your posts on Facebook for a while now, and I’ve been wondering if I should post my situation, which really isn’t very complicated. It is more like a question that belongs in a “Relationships 101” class, but I would like some advice.

I’m a 50-something male who has lived a single life and have been mostly content to do so, but a romance in my life would be good. I’ve been attracted to the same friend for 11 of the 13 years I’ve known her. I did suggest once years ago going out in a friend way, but she politely deflected the question. But we’ve socialized happily within a group all this time and do occasionally spend time together, just she snd I. I’ve never told her directly how I feel about her. Has she guessed? I’ve no idea.

Ten years on, we are still in the same social group, and that’s not likely to change; neither of us looks likely to move away. Everyone else I know as well as I do her name drops their individual partners from time to time, if there are partners. She never has done this. Does that mean she is just a private person, or a long-term single like I am? If I knew she had a partner, I could move on, as I have before with other women. But as things stand, I have some doubts about my choice to stay silent. I recently had a brief hospital stay and though mine was a non life-threatening issue, it gave me some “life is short” thoughts.

So here is my question, which I’d like to turn around so you can imagine being in the situation. If you had a friend—-good but not a best friend—-who was secretly and strongly attracted to you, would you want to know? Say you’ve never thought about the person in a romantic way, but you do like the person. Would you mind knowing, or would you prefer they kept it to themselves, so the friendship isn’t “complicated”? — Longtime Friend

Putting aside for a minute the oddity that you don’t know whether a good friend of yours for over a decade has a partner or not, I want you to know that your secret attraction to her probably isn’t as secret as you think. From the moment you suggested “going out in a friend way” all those years ago, if not before, your pal has at least suspected you might be attracted to her. That she politely deflected at the time and has never, in the years since, shown any signs of interest in you – at least not that you mention – and has never flirted, or seemingly encouraged you in any way to romantically pursue her suggests that her feelings for you are not the same.

Assuming your friend has never given any sign that she’s interested in you, I think it’s safe to assume that she’s not. And then the question shouldn’t so much be whether she would want to know your true feelings for her, but whether you stand to gain more than you might lose by expressing your feelings for her. And you know who might be able to shed some insight? A mutual friend. Is there anyone in your social group you could reach out to and ask for guidance? This could be as easy as saying, “Hey, Carol never mentions a partner. Am I right to assume that she’s a longtime single like I am?” The tone and content of their reply could answer a lot of questions without your even having to directly ask them.

Finally, I can appreciate a hesitancy in potentially scaring away or offending or embarrassing a longtime friend by expressing interest that might not be wanted. This is definitely a risk you have to weigh. But as long as you’re respectful and not a creep about it and accept whatever response you get and never push for more than a platonic friendship with her again if she doesn’t indicate she wants that, I don’t think this would be something that would have to end the friendship. Regardless, I would urge you to start looking outside your friend circle for potential dates though. If you genuinely want romance in your life, and you’ve recently had an experience that reminded you that we’re here for just a brief time, maybe the answer isn’t to pursue someone who, in 13 years, hasn’t shown interest in you. Maybe the answer is to look in new places.

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. Anonymousse says:

    You asked her out and she deflected. Ten years have gone by and you are no closer to her as a person. You don’t even know if she has a partner, which to me, indicates you anre not close friends at all. Assume she is not interested.

    But also why have you waited 13 years?

  2. You made a cowardly error over a decade ago, when you asked to go out ‘in a friend way’, when you really wanted a date. Although this speaks poorly of your courage and maturity at that time, I think she would have accepted, if she had any interest in you. I agree that she recognized your offer for what it was. Since she declined, she also knows that the ball is in her court if she acquires a romantic interest in you. I can only assume that she hasn’t, since she’s given no signal to you. You asked once, albeit timidly. Any possibility you might have had is long past. Get it out of your mind or you are going to have difficulty in your friend group going forward. Strange to go over a decade, before considering a second approach. I think that is the rational part of your brain telling you that her answer is 100% likely to be ‘no’ and that it is likely to be awkward.

    If you are now interested in romance in general, then you need to broaden the circle of people you associate with or try on-line dating. This friend isn’t the answer to your quest for romance.

    1. Heidi ODaniel says:

      Don’t do it. I have taken friendships as a sign that someone was interested in me. That great longing for love. Every time I told the person that I had feelings for them, it backfired and they no longer speak to me. Please don’t ruin your friendship for a rare chance she feels the same.

  3. LisforLeslie says:

    You’re thinking about what you want in life – that’s wonderful. But you’re taking the laziest route possible to find romance. Look, if things were meant to be with this woman, they would have happened sometime in the last 11 years.

    If you want a relationship do a little work and go find groups: Book clubs, hiking, movies, take a class at a local university. Whatever is close by. Try MeetUp to find things that are happening in your community. Then go. Go to participate and meet some new people and I bet there will be women who have a similar goal of meeting men. Maybe it works for you, maybe it doesn’t but you will meet new people. You won’t upset the balance of your existing group friend and you’ll hopefully get a nice hike or movie out of it.

  4. You mentioned that you two spend time together. Ask her again .

  5. Christine says:

    I disagree with many of the other commenter. 10 years ago is a long time. Maybe 10 years ago “stuff” was going on in her that made her deflect your invitation. I’ve been there. To me, if you’re prepared for rejection, you have nothing to lose.

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