My friend has hated everyone I've dated

Thursday | June 5, 2025

Love Letters Relationships

My friend has hated everyone I’ve dated

For those who signed up for the movie: if there is room for you to get tickets, you’ll be emailed in the next few days. I’m trying to get as many people in as possible, and a lot of people signed up. If you do not hear from me by Monday, there was not room (sorry). But I promise, there will be more fun things to sign up for.

Dear Meredith,

I’m writing because I’m torn and unsure if I made the right decision.

I’ve had a male best friend for the past 15 years. He’s been there through so much of my life — family stuff, heartbreaks, big wins, and all the in-betweens. But there’s always been one constant: he’s never liked anyone I’ve dated. Not one. He never even gave them a chance. He’d point out their flaws before meeting them and flat-out refused to be around them. It always made things complicated and tense.

Now, I’m in a serious relationship. For the first time, someone I’m with said what I always feared: “It’s me or him.” My boyfriend gave me a clear ultimatum, and I chose him (my boyfriend). Not because I was forced to, but because I finally had to confront something—why has my best friend always had such a problem with anyone I love?

My best friend has never been in a relationship, not once. And while I don’t want to believe he stayed in my life for the hope of something more, I can’t help but wonder. Is that why he couldn’t accept anyone I was with? Why he made it so hard?

I didn’t want to cut him off. But he’s left me no choice by refusing to even try. Did I do the right thing by choosing my partner? Or did I give up on a friendship that meant something—maybe not romantic, but still deeply real?

Do men really stay close to women they’ve known for years because they think one day there will be a chance?

– Torn Between Two Truths

You did the right thing, it seems.

If you had dropped your friend because of your boyfriend’s ultimatum, I might have concerns. But you made your own choice, one you knew was coming.

To me, gender doesn’t have much to do with this. If you had a straight woman friend who behaved this way, you’d still be asking, “Why are you mean about this part of my life?”

Let’s say your friend is attracted to you and has been waiting around this whole time. If that’s the case, it’s best that you walked away. Also, if that’s his real motive, he has been doing a bad job of making this happen. Why would you fall in love with a friend who was mean about the people you like? Wouldn’t he want to date some people to learn about relationships/show you what you’re missing?

It’s possible this is more about the status quo. Maybe he’s a guy who doesn’t like change. Perhaps he enjoys bing single and wants you to be single, too.

I do hope you told him why you had to let go, and how you feel about all of this. I hope you communicated – very clearly – why his history of disapproval has hurt and confused you. I also hope your boyfriend would be open to the relationship if your friend showed up having done some personal work. If this friend says, eventually, “Hey, I get it. I have made this unpleasant, and I’d hate to lose you because of this,” well, I hope you can work on it.

But for now, this is the status quo you seem to need.

One last thought: if your boyfriend finds reasons to give ultimatums about other friends (or activities, choices, etc.), throw up a flag. Not to sound like your friend, but that would be a problem.

– Meredith

Readers? Is the ultimatum its own red flag? Would you ever ask a partner to drop a friend? Thoughts on a man who doesn’t want his friend to date anyone? Thoughts on that last question about men waiting around for women friends to fall for them?

What’s on your mind about friendship, love, exes, dating, love, loss, crushes, marriage, etc.? Submit your letter by using the anonymous form, or email [email protected].

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Featured Comment

You sure gave this “friend” a lot of power over your dating history. But he was never a friend. He might have been jealous or selfish or punishing you for getting out there to date when he couldn’t but someone who unilaterally rejects the people you date based on nothing before ever meeting them is not a friend.

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