First of all, I’d like to start by saying that I have no reason to believe that my girlfriend has any hidden intentions with this guy. She’s a genuinely good person, truly one of the kindest and most loving person I’ve ever met, and we have a very healthy relationship. Now onto the friend…

He’s in his late 50’s. They met like 10 years ago (well before we started dating) at a coffee shop where they both worked part time. She disclosed their friendship to me very early on in our relationship, and while I expressed concern about his age, I told her I’d accept their friendship on the basis of trust and honesty. However, since then, I’ve caught some things that have kept me suspicious.

I’ve seen text conversations between them and I noticed he jumps at any and every opportunity to compliment her. He frequently compliments her physical appearance and her personality traits. He’s constantly using heart emoji’s, kissing face emoji’s, heart eyes, etc. I pointed this out to her and she says this is just how he texts. She told me he once said he would date her if she was older. For context, he was complaining about his failed love life and said something along the lines of “If only you were older…” Again, I pointed this out, and she didn’t think anything about it.

For years she kept insisting that I finally meet him so I gave it a shot. Within minutes of meeting him, I can tell something was off about the guy. He seemed kind of whacked out. He spoke fast and very loud. He was jittery, and just all over the place. He told a story about his friend who started sleeping with 18 year old girls. He referred to the 18 year olds as “so beautiful and so gorgeous” seemingly glorifying the fact that his much older friend was sleeping with teenagers. He then randomly commented on how women look “so hot” yoga pants. I def caught some creeper vibes from this guy and I told my gf but she disagreed and said I just don’t understand him and their friendship.

Fast forward a few weeks later, I saw her text messages from the day we met up where she told him I was still undecided about meeting him. His response was “ha ha, tell him if he doesn’t hurry up, we’re going to get married.” This was the final straw for me.

I want to ask her to cut her friendship with him and I’m almost sure she will, but I’m afraid she will resent me for this. She’s told me he is a very important person in her life, that he’s been there for her through some of the roughest times in her life, and that she feels bad that he has no friends or family. On one hand, I would feel bad for taking this friendship away from her but on the other hand, I think he’s been testing the waters and she’s totally oblivious to it. With all of this in mind, I’m weighing out the following options:

Option A: ask her to cut all contact with him
Option B: remain friends but no in-person contact
Option C: accept the friendship under the understanding that realistically nothing romantic will ever come out of it

What do you guys think is the appropriate course of action given the situation at hand?

TLDR: GF is long time close friends with a guy old enough to be her dad. He’s too friendly to her for my comfort and has made some inappropriate jokes and subtle comments about them being together. GF is oblivious. I want him gone, but I don’t want her to resent me. How do I go about this? Should he stay or should he go?

5 comments
  1. What about Option D: Your gf sets clear boundaries with this “friend” that she’s not comfortable with compliments, offhand remarks about them dating, kissy face emojis, etc. And she wants to make sure he understands that she will only ever view him as a friend; that she views anything else as inappropriate (and frankly creepy) given their respective ages. And that she also wants to be respectful towards you, her boyfriend, by keeping their relationship strictly platonic (aka no flirting whatsoever).

    Then whenever he tries to push her boundaries (which he will) she either calls him out on it or stops responding/distances herself. Honestly i think she might then realize that this guy isn’t all that interested in a friendship with her and just wants to live out some fantasy of being with a much younger woman.

  2. Dude that is odd she’s “friends” with a guy that old. You need to sit her down for a serious convo. Tell her this guy is in love with her. Explain all the evidence like the hearts on text, his marriage comment, etc. Say you don’t feel comfortable you being friends with him. He seems to be sticking around in hopes our relationship won’t work out and he will make a move. I would then ask her how would you feel if I had a friend that was older or younger that talked to me like he talks to you. Like if situations were reversed. See what she says. In the end your goal should be option A. Let her know you just don’t trust him. So please don’t talk to him anymore. You can tell her she can blame it on you. She can tell her friend that it’s “my boyfriend’s fault”. That will get the pressure off of her. Give her the other options if you want but let her know you prefer option A.

  3. Fuck that. She’s obviously enjoying the attention from an older man. Trust your gut, mate. Please. Don’t let yourself get walked all over.

    Set boundaries and be prepared walk away with your dignity. I promise you you’ll feel a 100% better about the situation.

  4. Option D.

    Leave.

    Tell her that as she can’t see he’s a creep, that you no longer want to be in a relationship with her.

    And tell her when the creep hits on her and things go south quickly with their so called friendship all she’s going to get from you is an “I told you so”

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