Hi everyone, I’m looking for outside perspective because I feel like I’m going crazy trying to figure out what’s normal and what isn’t.
I (M24) am in a monogamous long-distance relationship with my girlfriend “Emma” (F23). She’s bisexual, which I fully support — my issue is not her sexuality, it’s boundaries.
Emma has a best friend “Lily” (F23) who she has known for years. Lily has a boyfriend of about 10 years. The complication is that Emma and Lily have slept together in the past, and Emma’s ex was also involved with Lily at different points. Emma has told me she’s still adjusting to what a “normal” monogamous relationship looks like after being in a very open/toxic dynamic previously.
Since Emma and I started dating, Lily has constantly made sexual comments and “jokes” that feel completely inappropriate for a friend — especially one with sexual history.
Examples include Lily texting things like:
offering to bring her sex toys on trips “for you guys to borrow”
talking about wanting to be the one to make Emma “squirt”
saying things like “you wanna make her a mess”
referencing how she “got close with her” sexually before
This isn’t occasional humor — it’s repeated and explicit.
When I expressed discomfort early on, Emma told me I was being insecure. Later, she admitted Lily was the one telling her that this was “perfectly normal” because they had slept together before.
One of the worst moments was when I sent Emma a private message about how uncomfortable I was with Lily’s sexual comments, and Emma read it out loud to Lily. Lily responded with something like, “He sounds insecure, babe,” and Emma didn’t shut it down.
There are also other patterns that make me feel like Lily is emotionally possessive:
Lily likes almost all of Emma’s social media posts except the ones that include me
Emma posts lots of edits of her and Lily together
Lily gets weirdly competitive when Emma talks about intimacy with me
Lily refers to Emma in a possessive way (“my girl”) and they post very couple-y photos
Emma also went on a week-long trip with Lily (despite their sexual history), which really bothered me. I know if I went on a trip with someone I’d slept with before, Emma would not be okay with it.
The long-distance aspect makes it harder too. I’ve spent a lot of money trying to see her, and during arguments Emma has made jabs like, “I could spend money on a passport to come see you, but I’m putting it toward my trip instead.” Later she blamed those comments on trauma from her past relationship, but it still hurt.
Another strange thing: I once confided in Lily that I wanted to buy Emma her first piece of jewelry as something special. Lily went behind my back and bought her jewelry first, which felt like she was trying to insert herself into partner territory.
Recently, Emma has started to realize how inappropriate Lily’s behavior has been and admitted I wasn’t wrong. She’s noticing more patterns now and says she understands why it crossed boundaries.
But I’m struggling with the aftermath. I feel like I’ve been forced into the role of therapist or mediator, and like there has been a third person in our relationship dynamic this whole time.
My questions:
Are these reasonable boundaries to expect in a monogamous relationship?
Is Lily’s behavior inappropriate or am I overreacting?
How do you rebuild trust after your partner allowed a friend to undermine you and dismiss your concerns as insecurity?
Any advice is appreciated.
TL;DR: My long-distance girlfriend’s best friend (who she slept with before) keeps making explicit sexual “jokes,” acts possessive, and undermined me by calling me insecure. My girlfriend initially dismissed my concerns but now admits it was inappropriate. I’m struggling with trust and boundaries and don’t know how to move forward.