WIBTA for refusing to set up my close friend with another friend?

Over a year ago, my guy friend (who we’ll call Jack), who I’ve known for 8 years, had a 2-month talking stage with a girl (we’ll call her Anna) before he eventually friend zoned her, realizing that he wasn’t catching feelings, nor was he ready to get into a relationship. They agreed to stay friends, and Anna eventually grew close to me and became a member of our friend group. But she was still heart broken for months, so I’ve been there to console her as well as help her process her feelings and accept the situation.

It did not help that the two of them shared classes and were constantly together almost every day. I’ve seen Anna stress out and cry over Jack in addition to all of her personal issues. Sometimes she would tell me she was over him just to take it back within the next 3 days. It was so bad that getting away from him became a factor in deciding where she wanted to go for university. Jack suspected that she hadn’t fully moved on, but because she hid her feelings from him, along with the fact that he already communicated what he needed to, he was basically free of any responsibility.

Anyways, you can imagine my satisfaction when Anna finally started crushing on a new guy. The thing is, New Guy is friends with Jack, so she’ll often go to him for advice/information about New Guy. She’s been getting closer to New Guy for a few weeks now, and if you haven’t guessed it, Jack is jealous. He’s not sure why; whether it’s because he actually likes Anna or if it’s just because he’s losing the attention/validation. Either way, he wants her to know that he’s bothered, but doesn’t want to say anything outright. Anna’s noticed that Jack’s texts have been overly dry, and Jack wants me to hint to her that he might be bothered. I refuse to help him.

I think he wants what he can’t have, especially because he’s constantly hearing about Anna and New Guy. I think the moment Anna’s eyes are back on Jack, he’ll realize that his feelings towards her are still just platonic. I refuse to sabotage her progress with New Guy just to re-introduce more confusion, stress, and regret into her life.

On the other hand, Jack is very adamant that his feelings aren’t as shallow as I’m accusing them to be. He feels like Anna’s the only person/romantic option who accepts his weirdness, and while I applaud the vulnerability, I can’t help but wonder if this is all because he subconsciously misses the attention and validation he gets from someone liking him. Jack was also aware of this, but he’s just been getting more agitated over time and is now reconsidering his feelings for Anna.

Jack is one of my best friends. He says he’ll regret it if he doesn’t tell Anna how he feels, and that he’s scared Anna will get with his friend and he’ll lose his chance. I’d be a terrible friend not to take his emotions seriously, but I also want Anna to at least see things through with New Guy without having to think about Jack. WIBTA for abandoning loyalty for what I think is best?

12 thoughts on “WIBTA for refusing to set up my close friend with another friend?”
  1. NTA. Jack is the dog in the manger. He didn’t want the toy until the other dog started playing with it. If you help him ‘hint’ his way back into her head, you’re just helping him reset her progress to zero. If his feelings are real, he can use his big boy words and tell her himself, but we all know he won’t, because he just wants the attention back.

  2. None of this has anything to do with you so you should stay out of it. If he has something to say to Anna, then he can say it to her face. Putting you in the middle is immature and will only serve to cause drama.

  3. **NTA.** You’re not refusing to help your friend, you’re refusing to be the middleman in a messy emotional situation. That’s a pretty reasonable boundary.

    Anna spent months heartbroken over Jack and is *finally* moving on. It would be unfair to derail that progress just because Jack is suddenly feeling jealous now that her attention isn’t on him anymore. Whether his feelings are genuine or just a reaction to losing that validation, it’s not your job to test that theory with someone else’s emotions.

  4. LMAO if Jack is sure of his feelings, he should tell her. BUT THE FACT THAT he just wants *you* to *hint that he’s bothered* says everything.

    NTA, stay out of it and let him deal with it. This isn’t about loyalty or being a good friend. If he’s making if out like it is, then he’s not a good friend.

  5. NTA

    If he really wanted to be with her he would be already. He’s just got fomo and it would be a disservice to her if you supported his intentions here. Guaranteed he’d get bored instantly.

  6. NTA – he’s jealous he’s losing the attention. Don’t help him out. He’d happily have kept things as they were if she hadn’t moved on. Remind him of that.

    One suggestion I Would make is to tell Anne to maybe stop going to Jack for insight on New Guy since they (her & Jack) did have a form of a relationship for a while. I don’t trust he wouldn’t start giving her bad info / advice to sabotage the relationship

    1. Exactly this! She should just stick to New Guy and communicate with the person she wants to see things through with

  7. YWNBTA.

    I think you’ve clocked the situation perfectly: Jack doesn’t miss Anna, he misses being the center of her feelings. And as soon as he has her attention again, he’ll probably friendzone her for a second time. He had his chance with her and he wasted it. She deserves to enjoy her time with the new guy without having old feelings resurface.

    And even if Jack’s feelings were genuine, it should be him telling Anna, not you. The only thing you should tell Anna is to stop going to Jack for advice, seeing that they had been previously involved.

  8. NTA

    you’ve got no requirement to do so and that’s a situation you’re not going to want to be in the middle of.

  9. NTA

    But I understand why you feel the way you do.
    To play a little of devils advocate here, there’s a good chance Jack is either a late bloomer when it comes to realizing his feelings or he just plainly didn’t want to or didn’t dare to acknowledge them.

    Either way it’s his loss, if he wants her to know he’s the one who needs to muster up the courage to tell her.
    Be that it may result in a broken friendship or whatever. This isn’t something you should be involved in, you’re happy Anna has finally moved on, she’s crushing on someone else.

    If Jack keeps insisting on you telling her then he’s just using you to avoid the fallout that might happen.
    You are still loyal to both of your friends, just deciding not to be the carrier pigeon of 2 people that are 2 meters apart.

  10. Jack just wants to have sex with her before his friend can get the chance to if it hasn’t happened already. He doesn’t want to be one upped and these so call “feelings” he’s found for her is just him realizing he doesn’t have all her attention anymore and wants to just ruin her.

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