My (27F) boyfriend (28M) is obsessed with my ex (27M)?

Shirley Stafford Hours
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Picture a sunny grocery store aisle, where a chance encounter flips a couple’s “near-perfect” romance into a bizarre saga. For a 27-year-old woman, bumping into her ex with her boyfriend by her side seemed like a fleeting moment of polite chit-chat. But what started as a sarcastic quip from her boyfriend has spiraled into an unsettling obsession, with him worming into her ex’s social circle and lashing out with passive-aggressive jabs. Now, their once-cozy relationship teeters on the edge of a breakup.

This Reddit tale, dripping with tension and red flags, pulls us into a drama where insecurity and manipulation collide. As her boyfriend mimics her ex’s career, crashes his virtual hangouts, and guilt-trips her over intimacy, she’s left humiliated and confused. Is this jealousy gone wild or something darker? Let’s unpack her story and figure out what’s driving this bizarre behavior.

‘My (27F) boyfriend (28M) is obsessed with my ex (27M)?’

We’ve been together for 2 years and before this, I would say our relationship was very close to perfect. At the beginning of the year though, my boyfriend and I were at the grocery store and we bumped into my ex and another friend. This was the first time they had ever met each other. We made polite conversation before going our separate ways.

My boyfriend made a sarcastic comment about how nice my ex was when he was out of earshot. I didn’t think much of it at the time. A few weeks after this, I noticed he was on my ex’s Facebook page. When I asked him what he was doing, he shrugged it off and said he was curious because he saw my ex had commented on Luke’s (a mutual friend of ours and my ex’s) post.

He’s since friended him on there and claimed my ex was the one to initiate it. He’s followed him on Instagram and twitter too. He comments on a lot of his posts too but my ex rarely comments back. He also somehow got Luke to invite him to my ex and his friends’ weekly (virtual) hangouts.

I mentioned I found it weird that they were hanging out but he dismissed it and said it wasn’t a big deal. He’s also started talking about changing his career path to what my ex is doing and makes snide comments about if his dad paid his way for him, he could take me on fancy trips too.

He’s also become incredibly passive aggressive towards me and makes comments about how if my ex didn’t move abroad for a few years we probably would never have dated. If I say no to anything (including s**) he comments about how he bets I wouldn’t say no if my ex was the one asking. He also got really sulky when he realised I still had a gift my ex gave me.

Yesterday we had a massive fight over it because I wanted to spend time together, but he ditched me to go hangout with my ex. I got so upset I told him he might as well date my ex instead. I don’t really know what to do now. He’s giving me the silent treatment and I heard him tell my ex what I said which is really humiliating.

What can I do to make him stop hanging out with my ex? TL;DR – My boyfriend is weirdly obsessed with my ex and has gone out of his way to join his friendship circle. He’s also become passive aggressive towards me since spending more time with him.

The OP’s dropped an update on the saga—curious? Click here to check it out!

When a partner fixates on an ex, it’s rarely about nostalgia—it’s often a neon sign of insecurity. This boyfriend’s behavior, from friending her ex online to mimicking his career, screams a need to compete, but his passive-aggressive comments and sulking reveal a darker edge. Dr. Lundy Bancroft, an expert on abusive relationships, warns, “Manipulation often starts subtly, testing boundaries to see how much control can be gained” (Lundy Bancroft’s website). His book Why Does He Do That? could be this woman’s roadmap.

Her boyfriend’s actions—guilt-tripping her over saying “no” to intimacy, shaming her publicly, and prioritizing her ex over their time together—point to emotional manipulation. He’s not just jealous; he’s punishing her for his insecurities, using her ex as a weapon. Her attempt to set boundaries, like calling out his obsession, was met with silent treatment, a classic control tactic. This isn’t love; it’s a power play.

Zooming out, this reflects a broader issue: how insecurity can fuel toxic dynamics. A 2019 study in Personality and Social Psychology Bulletin found that insecure partners often engage in “mate-guarding” behaviors, like monitoring or belittling, to assert dominance (Sage Journals). Here, his obsession with her ex seems less about admiration and more about proving he’s “better,” at her expense.

She needs to set firm boundaries, starting with a calm but clear demand for respect. Couples counseling could help, but only if he’s willing to own his behavior—per Dr. Bancroft, refusal is a red flag. If he escalates, she should lean on trusted friends and consider resources like LoveIsRespect.org for guidance on unhealthy relationships. Readers, have you dealt with a partner’s jealousy turning toxic? Share your thoughts below.

Here’s the comments of Reddit users:

Reddit didn’t mince words, dishing out a mix of alarm and wit over this boyfriend’s antics. Here’s the community’s spicy take:

joe-dirt-1001 − If you want to be so much like my ex, I will just break up with you too.

econgirl7 − Hey, um, so, you mention that your relationship was 'close to perfect' before this, but considering 'this' started nearly a year ago, this new dynamic characterizes almost half of your two years together. Sounds a lot like he had on a honeymoon period mask and has now revealed his true colors.

Sorry, but I don't think 'getting your bf to stop hanging out with your ex' solves your problem. Your current boyfriend has serious issues and is demonstrating a willingness to try to build himself up by tearing you down. He also is apparently pretty manipulative and controlling.

So many red flags: * He's managed to make you rethink ever saying no to him because you're trying to avoid a manufactured fight in which he compares himself to your ex.. * He sulks to get his way.. * He guilts you to get his way by saying you probably wouldn't say no to your ex. * Passive aggressive, etc.... It appears he's testing your boundaries to figure out what emotional manipulation he can apply to get his way.

He's 'punishing' you by weaponizing things you say while discussing your relationship with him and telling them to others to shame you and make you less likely to advocate for yourself later. * Kind of sounds like he's trying to make you jealous to prove you love him more (possibly stemming from insecurity, but could be more malintentioned than that)?

Constant testing of affection is not a great strategy for longevity....* He's insincere. The two-faced thing he has going on with snide comments about how *nice* your ex was, and making fun of the opportunities/connections your ex had in his career at the same time as he's trying to build a relationship with him (to leverage his career connections?) is definitely going to catch up with him.

The way you describe it, it's deeply creepy how he manipulated his way into your ex's friend circle. I'm sure you want back the boyfriend you thought you had prior to this revelation, but he probably doesn't exist. This is who you're dating. Even if you get him to stop hanging out with your ex, he's demonstrated how he interacts in relationships once he's made it to the comfort level

He will use what he learned through this period to get you to think it's too much of an inconvenience to stick up for yourself in other ways. Please don't buy into the sunk cost fallacy... you've got too much of your life still ahead of you for that. Don't take my word for it though. I highly recommend you read Lundy Bancroft's 'Why Does He Do That?' I think you'll recognize your boyfriend.

yikesyikes777 − Red flags all around. It sounds like your guy is deeply insecure and channeling that insecurity into loathing. He's already taking it out on you. Manipulating you, pressuring you in the bedroom, even attempting to turn your seemingly amicable ex on you?

He's pushing your boundaries. And his demands are impossible. Nothing you do will fix his insecurity, and so he will continue to lash out and demean you. I know because I have been there. This relationship sounds nothing 'close to perfect.' I sincerely hope you distance yourself from him and get some perspective. Best of luck.

Countess_Sardine − Your boyfriend is clearly going through some things that he's not prepared to discuss with you like an adult, so I'd take this to a couples' counselor.. If your boyfriend won't go? D**p him. You deserve so much better than this.

Captainsblogger − To be honest this sounds frightening.

tangerine-trees- − I dunno man, I don’t think I’d even want to date someone who reached this level of stalker obsession with my ex. Maybe it’s for the best to just end things, he clearly needs professional help for his insecurities. I don’t think a relationship is healthy for him right now.

msxlk − The s** thing is a huge red flag, if someone is manipulating you into having s** by making you feel bad, you need to take care of yourself and leave this relationship, maybe they'll end up dating each other lol

samiirose52 − He's acting out based on his own insecurities and it's obviously gotten deep. You need to establish a boundary with it and reassure him you love him for being him, not for being like your ex... Who you're no longer with for a reason.

rydendm − he already turned into a monster. It's like he wants to be him or something, then m**der him on a boat trip.

[Reddit User] − Holeee shite. This has gone way overboard and I wouldn't be able to respect and keep dating someone this mentally unstable. I think it's time to walk - for your own sanity and safety.

These Redditors smell trouble, from manipulation to outright creepiness, but are they onto something? Is this a case of insecurity or a deeper power trip?

This story is a rollercoaster of red flags, leaving us wondering if this boyfriend’s obsession is a quirky phase or a dealbreaker. One thing’s certain: no one deserves to be a punching bag for their partner’s insecurities. What would you do if your partner got cozy with your ex? Have you ever faced jealousy that crossed the line? Drop your thoughts below and let’s untangle this messy love triangle.

For those who want to read the sequel: [UPDATE] – My (27F) boyfriend (28M) is obsessed with my ex (27M)?

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