• Keeping Friends

Falling in love with a best friend

Published: February 20, 2016 | By | 8 Replies Continue Reading
A young woman asks about how to handle falling in love with her best friend.


Hi Irene,

Hey, I’ve been best friends with this guy for five years now. I’m starting to feel different about him. I’m so scared to tell him because I’m afraid it might ruin our friendship.

What if he doesn’t like me back? All my friends say we would make a good couple. How do I tell him? Help!

Signed, Jen


Hi Jen,

Getting closer to a friend, whether its platonic or romantic, always involves taking a risk. The other person may not feel the same way you do.

Since you’ve known this guy for quite some time, the odds are on your side. You probably have a good sense of whether he’s already involved with anyone else; whether he might be receptive to your overtures; and whether he has expressed anything other than a platonic interest in you.

If you’re willing to take the risk, tell him that you have really treasured your friendship and don’t want to do anything to damage that—but you want to be honest with him about your feelings. Reassure him that if he doesn’t feel the same way, you hope that nothing about your wonderful friendship will change. Then hear him out.

Let us know what happens.

Best, Irene

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Category: Creating and maintaining boundaries, KEEPING FRIENDS

Comments (8)

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  1. CassieO says:

    I know exactly how you feel. Please someone tell me what to do about a guy best friend who has blurred the lines with me. As soon as we met, I knew he had fallen for me. Well, I fell for him as well. He boosted my self esteem (I had been in abusive relationships), and he was so kind and caring. We have known eachother for 10 years. We flirt a lot, admit we like eachother but he has a girlfriend — one that treats him awful and he knows it. :(( but he won’t leave her… Yet. She may even be seeing someone else on the side. I have stood by him knowing how hurt he is. Suddenly it seems like he can’t talk to me… Like he’s not allowed. He has dropped off the face of the earth but yet when I do see him for a few minutes , he is great! We pick up where we left off. Our texting is nonexistent now, no more laughing , chatting… He has no time to see me so I can’t get answers. What do I do with this friendship???!:((

  2. Maddie says:

    I believe when men are truly interested, you know it. A man who wants a romantic relationship would have acted on it in the time span of five years.

    Once you let him know you want him as a boyfriend and he does not feel the same way, you can kiss the friendship goodbye. Sad but true.

    It’s a fallacy that interested men are too “afraid” to act on their feelings. Men who want something more let it be known.

    Good luck.

  3. Therese says:

    I think about this in a different way than most people, having been in your friend’s position a few times.

    I think it is emotionally dishonest to not tell your friend you carry a torch for him. I’m not saying you need to tell him with the expectation that he will want to take the relationship to a different level, but so that you can both be on the same page as far as your relationship is concerned.

    Imagine how he would feel if he found out five years from now that you’ve been in love with him? Whether that makes him happy because he feels the same way or sad for you because he doesn’t return those feelings, I feel like some trust would be lost because you kept something pertaining to your relationship secret from him.

    In my past friendships it has made me question the motivation of my friend when I have only been told months later that they’ve known they have feelings for me. Right or wrong, it makes me wonder if they still would have been my friend if a potential relationship weren’t on the table.

    I feel like you owe it to your friend to be honest, so that he knows you value his place in your life regardless of the form that takes.

  4. Amy F says:

    Many healthy long term relationships began as friendships, but there is also the risk that romance can ruin a friendship. You can’t unpop a balloon.
    If you love him romantically and don’t say anything, can your friendship survive if he were to fall in love with someone else? Could you be truly happy and supportive of that romance? Could you continue to be an unselfish friend without destroying yourself in the process?
    What if you say something and the feelings aren’t mutual? That could change your friendship forever too, because you can’t unpop that bubble either.
    And what if he feels the same way as you do, and you go on to have an epic romance and live happily ever after?
    I’m posing these questions in dramatic fashion. You can’t know how the future will turn out. can usually tell when someone feels romantic toward me vs friendship, so it’s possible he already suspected.
    My advice would be don’t do anything rash. There’s no need to rush into a decision.
    Good luck.

  5. Lisa says:

    Jen, you will need to be honest with your friend since you are already honest with yourself. If you don’t take the chance you will never know what could have been. Life is a risk and I can’t think of a better risk to take than LOVE. Life is short, go for the gold!! My best to you. Please keep us up to date.

  6. Cecilia says:

    “Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

    Take a chance. Tell him! I guarantee you will regret it someday if you don’t tell him.

    Good luck!

  7. Sandra says:

    Wishing you all the best, too. I absolutely agree with everything Irene says. You’ll feel better if you’re honest about your feelings — and it’s likely that he senses them. If you’re willing to deal honestly and fairly with the consequences, either way, then it’s worth the risk. Let us know what happens — and good luck!

  8. Ben says:

    It must be very scary indeed. There is an old saying that I have found true, “It is better to have loved and lost than to have never loved at all.” Life ain’t easy. Decisions ain’t easy sometimes. Risks and benefits. Maybe make a list of pros and cons. Weigh the pluses and minuses. I hope personally that you risk and speak honestly with your friend. He might be feeling the same way about you… ALL THE BEST!!!

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