friendship, relationships

Should I Tell My Best Friend I’m in Love with Him? Or Should I Check My Feelings?

Hey T!

I’ve been in love with my best friend for most of our friendship, but we’ve never been able to actually have a relationship. We’ve actually been friends since first grade and now we’re both in our 30s. He was the first person I came out to, and even my very first kiss. We’ve messed around before, had threesomes, and even talked about the possibility of us having a relationship, but I don’t understand why we’ve never taken it to the next level.

What makes things worse, he has a tendency to date dudes that are way too similar to me. They’ve even had birthdays, days apart from mine. His boyfriends will either get jealous of our friendship or reach out to me to get advice on dealing with him.

His last two relationships were with two guys we were just supposed to be friends with and then he started dating them behind my back, only for me to find out later and then be forced to deal with the relationship and play the background.

Why does it seem like I’m always the rebound after he breaks up with these similar dudes? Do I need to end this friendship once and for all? Or do I just need to get my feelings in check?

– Dafeon

Dear Dafeon,

Thanks for writing to me. The situation you described is one that serves as the plot for countless stories in the entertainment industry. Movies like Love and Basketball and Brown Sugar are perfect examples of what happens when friends become lovers and then life partners. Then there are television shows with characters like Jim and Pam (The Office) and Dwayne and Whitley (A Different World), that also glamorize how friendship can blossom into a fairytale romance. And while these examples reflect what you’ve got going on, your situation is most reminiscent of another television show, Insecure.

In case you’re not familiar with the HBO hit, there is a character Molly, who similarly to you, is messing around with a best friend. It’s clear she wants more, but her best friend Dro is either clueless to that fact, or unwilling to give her more. And she finds that extremely problematic. In light of her frustration, at the start of this current season she tries doing what I believe you should do in your own situation; which is, set some boundaries.

I know everyone likes to pretend to be carefree and chill about everything, but at the end of the day, most people don’t subscribe to that kind of lifestyle. Most folks, such as myself, like to have boundaries and the ability to categorize people and relationships.  So if you don’t want feel like your friend is benefitting from all of the perks of a relationship (intimacy, sex, and your loyalty), yet unable to officially commit to you like you want, then it’s up to you to say something. You have a duty to yourself to gain clarity on the nature of your dynamic between you and your friend.

Suggestions going forward.

  1. It’s time you boss up and have a conversation with your bff . Be honest about your feelings for him. Tell him you love him more than a friend and see if he feels the same way. While there is a chance he doesn’t reciprocate your feelings, at least you would have stated your peace and taken a step to get out of this state of limbo you seem to be in.
  2. In the case your best friend doesn’t love you in the way you do, that’s when you need to establish some boundaries with him. For example, you two would have to agree that sex with one another (including threesomes) is off the table. Also, if he doesn’t love you romantically, you’re entitled to put your friendship on pause until you can shake off your feelings for him. It’s perfectly normal for friends to take a timeout occasionally. Many times these breaks occur naturally anyway without conversation. That doesn’t mean the friendship is necessarily over. It just means one or both people in the friendship need space to grow and evolve.
  3. If you find your friend does feel the same way about you after you two have a conversation, I would encourage you both to take things slow before jumping into a full blown relationship. While you two have been friends, you two haven’t dated. So take time to date one another and see what that is like before you head to the alter.
  4. Don’t ever put yourself in a situation where you feel your friend is abusing the relationship. Where you feel you’re putting more in than you ever get out. In other words, don’t constantly play the role of someone’s rebound if that’s not a role you enjoy playing.
  5. Lastly, I understand I pretty much have told you to speak up and put yourself out there. However, that’s because I realize the difficulty in trying to just shut off your feelings for a person. Also, you two seemingly have sex on occasion anyway, so the water is already muddy here. The vibe in your letter is screaming you want clarity, so just swallowing your feelings here is not in your best interest.


As always nothing but love,

Tavion Scott

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4 thoughts on “Should I Tell My Best Friend I’m in Love with Him? Or Should I Check My Feelings?”

  1. Rashid Darden says:

    T, this advice is spot on. I especially liked this part: “Also, if he doesn’t love you romantically, you’re entitled to put your friendship on pause until you can shake off your feelings for him.”

    I have done this before. In one case, it has worked out very well. We do acknowledge that the deep emotional bond we share didn’t originate as platonic love, but without that timeout, we wouldn’t have what we do.

    Now there is also the other end of the spectrum. Some “friends” don’t want you unless they can have all of you all the time. Those are the friends you gotta get rid of.

    1. AsAccordingToT says:

      Thank you for your kind words and nuggets of wisdom. and I appreciate you sharing. Not everyone is brave enough to have that conversation with a friend. By the way, I’m still waiting on the fourth installment of Lazarus. Lol

      1. Rashid Darden says:

        Stay tuned! You won’t be disappointed. 🙂

        1. AsAccordingToT says:

          No lie, I am extremely excited to read. You are incredibly gifted as an author

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