I’m 31F and my boyfriend is 29M. We’ve been together for 3 years and we’re serious—this summer, we’re supposed to move in together. But something from his past is making me uncomfortable and question how he handles boundaries with women.
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Timeline: When he was dating his ex (let’s call her Kate), her best friend was Amy. During a fight—when Kate gave him the silent treatment—he reached out to Amy to “check on Kate.” Kate later found out and confronted Amy while they were still together, saying it wasn’t okay. According to Amy, Kate even said: “If you two are so good together, why don’t you just date?”
After the breakup: During COVID, Amy was posting about being mistreated by her mom. My boyfriend (let’s call him Daniel) slid into her DMs to “check in,” and they reconnected. He later helped Amy move from DC to New York City. Amy’s mom gave him a TV and started calling him her “son.”
They weren’t close after that, but stayed in contact: He’d reach out to Amy when visiting NYC and meet up at a coffee shop. Amy would reach out when she was in DC.
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The dinner:
Recently, I had dinner with Amy, and it was extremely uncomfortable: She touched Daniel’s arm repeatedly. She said (verbatim): “We used to wrestle in my apartment. You wouldn’t win—even if I’m only 95 pounds.” It felt sexually suggestive and inappropriate. She brought up personal facts about him (like how he used to shave his head). She called Kate “crazy” and “controlling”, and spoke very disrespectfully about her—despite once being her best friend. She also said Daniel had been hurt by Kate, framing herself as someone who understood him better.
Daniel didn’t say anything to stop this or set any boundaries. He just awkwardly laughed.
When I brought it up afterward, Daniel said they didn’t wrestle—she pushed him once, but that was it. He said he was just trying to be polite and didn’t want to make things awkward. He previously called her a gold digger and he said he only wanted me to meet her because she’s a “relic” from his past and his friendship with her is like “watching the Titanic sink”—because she had a fake British accent and constantly made a spectacle of herself with superficial name dropping convos.
Despite all of this, he kept seeing her occasionally when in NYC, and I only found out the full extent of their history after I asked.
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TL;DR:
My boyfriend (29M) and I (31F) have been together for 3 years and are supposed to move in together this summer. Years ago, during his previous relationship, he reached out to his ex’s best friend, Amy, during a fight. After the breakup, he slid into Amy’s DMs, helped her move cities, and stayed in occasional contact with her. I recently met Amy and she behaved inappropriately—touching him, saying they used to “wrestle,” trash-talking his ex, and suggesting he was emotionally wounded. He didn’t shut any of it down. When I brought it up, he brushed it off and said they never wrestled—she just “pushed him once.” Now I’m wondering if I’m ignoring bigger red flags about boundaries and judgment.
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Does it seem like my boyfriend has poor boundaries, or is this just awkward history he failed to clean up?
Should I be concerned that he didn’t push back or speak up when Amy disrespected his ex and acted inappropriately in front of me?
Is it a red flag that he downplayed their history and only gave me full context when I asked directly?
Am I over analyzing this? 😅
Comments
He likes having two women fight over him.
Amy is the common denominator in his relationships failing.
Take your dignity and go.
Is this the ‘man’ you want to invest your future in when he can’t even act normally around other women.
He’s not trustworthy, he’s not loyal and he’s not husband material.
If you want to remain in a trouple with him and Amy then stay. I’m sorry but you are to grown for this teenage drama. Why are you conflicted?
The fact that you’re still in this relationship is a red flag, even bigger red flag you’re considering moving in with him? Even worse you’re making excuses for a grown man in his 30s. Doesn’t know what flirting is??? Can’t understand boundaries?? C’mon girl. How can you say that with a straight face???
He knows what flirting looks like. He likes it. You’re underreacting to his behavior.
“Not knowing what flirting looks like” is a crazy thing to say… and if Amy is a “relic” from the past and he doesn’t value her fRiEnDsHiP, why are you bothering having dinner with her? Clearly they still talk enough to schedule plans? That part doesn’t make any sense to me
I think there are red flags to be sure.
Kate was definitely controlling, silent treatment is a time honored abuser tactic after all, though there are non-abusive contexts where it’s simply cruel. Reaching out to your partner’s close friend is a very sensible thing to do, though maybe Kate just didn’t want Amy involved.
I can understand your boyfriend not wanting to make things awkward when Amy was clearly hitting on him in front of you (birds of a feather I guess). To me, the biggest red flag is how he called her a gold digger, a relic of the past whom he wanted to introduce you to watch that ship sink like the Titanic. I cannot imagine describing any friend in those terms, much less someone who not to long ago he was enthusiastic about seeing. Why waste time with someone if you think of them that way? And why would she be flirty with him in front of you?
Having female friends when you’re dating a woman is fine, as is hanging out with them alone. In a trusting relationship, this is a non-issue. To me, the open misogyny in the way he talks about Amy to you is the biggest red flag, as if throwing sexist slights is supposed to calm you down. Has he expressed similar misogyny in the past? Or any comments that felt off?
His defense of her as a relic would frankly make it hard for me to trust him. He is not responsible for other people’s choices, but Amy’s open flirting suggests either she has a poor sense of boundaries or they have something between them. Or possibly both. Neither would surprise me.