Hi Captain,
A friend of mine admitted near the beginning of our friendship that I (she/her) resemble an ex-girlfriend of his. I didn’t realize at the time how infatuated he still is with her, despite his protests to the contrary. He’s currently in a decade+ long relationship with his fiancée but still mentions the ex often. The resemblance was brought up in the presence of a mutual friend, and we laughed about the doppelganger resemblance. I was, I think understandably, rather weirded out, but his behavior at the time was above reproach.
Fast forward to deep in the pandemic. He and his fiancée moved across the country, and were isolating in accordance with CDC guidance (this was pre-vaccine). As a result, they hadn’t met many people in their geographic area, so our group of friends had been keeping up with them virtually once a week. We’d been discussing trying some virtual games online, and I’d found a site for us to try. He suggested testing it out the night prior to one of our weekly meet-ups…he then used that time, after testing out the interface, to proposition me for a friends with benefits relationship. His fiancée was evidently not providing him the…usual amount of attention, and he was feeling down, lonely and frustrated, and he had always found me physically attractive. I turned him down, kindly, and talked with him about other ways to resolve things with his fiancée or ways for him to find ‘fulfillment’ without putting himself or his fiancée at significant risk during the pandemic. He hoped that we could still be platonic friends, and asked me not to tell our mutual friends since they are more traditional, and I acquiesced.
At this point I should explain that he and his fiancée had had many conversations about him finding physical fulfillment elsewhere while she’s busy in her new job. She eventually acceded to his request. He explained this prior to the proposition. I should also explain that I don’t pass any judgment on people who have opted to practice ethical non-monogamy, though personally I prefer my relationships to be of the committed, monogamous variety. FWIW, he knows I am a single woman.
To his credit, he told his fiancée what transpired the next day, and she texted me apologizing profusely on his behalf. She seemed fine with what he was looking for, but not that he had “made me uncomfortable”.
Captain, I am shocked at how hurt and betrayed I am by his request. I’ve had friends ask me out who I’ve remained friends with, once we got over the awkwardness and they demonstrated they didn’t fall into the post-ask guilt-trip / Nice Guy / she-did-me-wrong tropes. Why does this one feel different?
The next day, I snapped at him during the group video call after he put me on the spot to answer (what I considered to be) a stupid question (on a relatively benign topic). The week following, I berated him about a very expensive system that he had gotten me as a/an (unwanted) gift (several months prior). Our area had had a monumental utility system break down, which then affected the functionality of the gift. After doing my best to remediate the system (and having not just a bad cold, but concurrent terrible physical symptoms directly attributable to this broken system) I spent more than half of the price of the gift trying to fix an expensive system I did not want in the first place, in addition to at least 3 weekends fixing the d*** thing.
Perhaps I’m conflating my anger about said d*** thing and his proposition, but our friend group is now (understandably?) bewildered at my ongoing angry reaction.
It’s been half a year, I’m still angry with him, and I’m wondering if I’m justified in breaking off the friendship. I’ve reviewed my actions and I don’t think I “led him on” at all, not even the smallest modicum of potential interest. It feels like he betrayed our friendship by asking this unwarranted, unwanted question without ascertaining if I’m even remotely interested, and that he’s just “going for it” based on the fact that I look like a “second chance” with his ex-girlfriend. I’ve been questioning every interaction he and I have had, and the motives behind his actions.
So, Captain, can you please help me with some of your wonderful, clear-headed advice:
· Am I overreacting? Or just reacting?
· If I decide to African Violet this guy, what would be the best way to do it? Preferably with the least disruption to the group. What should I even say to the group when they ask?
·Does his fiancée have any blame to share here? The male friends I consulted on this are confused by my nice treatment of his fiancée, but I don’t think she should be held accountable for his actions.
Many, many thanks.
Hello there!
It is 100% okay to not sleep with OR be friends with someone who brings to mind the plot of Vertigo (Alfred Hitchcock, 1958).
Having a crush or attraction and speaking it aloud to a friend isn’t the worst thing in the world, but I think there are reasons that this feels different. Could it be the sense of objectification that was lurking from the start, now made explicit?
Probably you feel angry and weird because you got cornered and then blindsided by an obviously planned sexual proposition, wrapped in an unscheduled therapy session, and dumped in your lap pretty much as a soliloquy that focused entirely on him: His nostalgia-boner*, his sadness and lack of “fulfillment” at home, his long campaign of pressuring his partner into agreeing to an open relationship, his pandemic risk-management and convenience, etc.
Like, was literally any part of it about your desires or what he had to offer you? Seems sexy, can’t imagine how you resisted. [/sarcasm]
(*I assume every sexually active person likely has a Greatest Hits compilation in the old memory palace, but masturbation is free, my dude! No need to invite your friends!)

Chart in PDF form if you need to embiggen.
If “sad man seeks emotional, sexual surrogate” wasn’t enough, said uncomfortable ambush ended with you soothing and reassuring him, smoothing things over with his fiancée, and also agreeing to keep it all secret from anybody else who might provide you with some support and sympathy or at least a good cackle.
Present-day, is it the months-old proposition or is it the expensive MacGuffin in your house that’s making you so irritable whenever he’s around? Who knows?
He foisted an expensive, unwanted gift on you, a gift that turned out to be extremely high-maintenance, exactly like everything about this situation.
I wasn’t even aware that the Sharper Image catalog *had* an Extremely Doomed Metaphor section, but here we all are.
His advances felt weird and dehumanizing, and overriding your wishes with this gift also felt dehumanizing, it’s not unrelated. Still, you don’t have to split these hairs in order to make a good decision for yourself. Even if everything about him were on the up-and-up, even if the angry feelings were somehow unfair or disproportionate, they’re here, they’re real, and they aren’t going away with time and effort. Sometimes speaking an attraction aloud does “ruin” the friendship, and oops, sorry, looks like this is one of those times. He took a risk, it made you feel bad, and you still feel bad whenever you interact with him, and that alone is a good enough reason to call it quits.
If you do decide to try to repair the friendship, I think the way forward is to acknowledge how angry you still are. “Friend, I realize I’m blowing up at you a lot, and I think it’s because I’m still angry and uncomfortable about our conversation last year and on top of it, this expensive gift is a fucking nightmare.” From there you can decide what might make it better: Some space/a temporary break from the friendship? Assistance from him in removing/replacing whatever the thing is? A real apology from him that’s about what you need and not what his long-suffering fiancée will permit? If there’s something worth salvaging, if he wants to actually make amends, you’ll figure it out from there.
If you decide to end the friendship, being bluntly honest about how uncomfortable and angry you are is also the key, so you can walk away clean without feeling like you’ve left something unsaid: “I’ve tried hard to put it behind me, but honestly, I’m still so uncomfortable and angry about the time you propositioned me, and I don’t think the friendship has really worked for me since. I wish you and Fiancée well, but I’m going to end the friendship here.”
Try to keep it short, resist the urge to make an airtight case that he’ll agree with and accept, as that road only leads to more talking about him.
I predict that his first reactions will be along the lines of “But it was okay with Fiancée, so I didn’t do anything technically wrong!!!!!!!” and/or “Are you going to tell [mutual friends] what I did?”
This is a full-service advice blog so I offer you the retorts: “Well, the point is, none of it was okay with me, and I think ending the friendship is the right choice for me, so, take care!” and “Our mutual friends are obviously going to figure out that we aren’t friends anymore, and that will probably be awkward for a while, but I think everyone will manage. I don’t plan to bring up the ‘why,’ but I also think you should organize another way to hang out with the others from now on so we’re not all up in each other’s business at Game Night.”
The group already knows that something is wrong, and you don’t have to manage their entire experience re: This Dude. What do you need from your friends right now? Some grace, space, and circumspection where they don’t pressure you to make peace or explain? In that case, scripts could be:
- “You can probably tell from how punch I’ve been around [Friend], but we had a falling out a while back and ever since then things haven’t been the same.”
- “Sorry if it makes things weird for you, but I think the friendship has run its course.”
- “Eh, the friendship wasn’t really working, it was time.”
- “FYI, I’ve explicitly uninvited him from the stuff I host, so if you want to connect, you should reach out directly.”
Don’t disclose his private info to the others, but I beg you, do not take on the burden of making sure this guy’s feelings, his ego, his romantic relationship, and the rest of his social life remain completely unruffled. When your friend used the platform test for group hangouts as a pretext to proposition you, he didn’t seem to think about whether that would make everything weird for you (or his fiancée, good grief!). In the aftermath of parting ways, if he wants to shore up his friendships, he’s free to do that, the same way you’re free to invite group members to do things without him going forward.
His fiancée doesn’t deserve “blame” but it’s okay to not be friends with her, either. She can be both a good person and not your friend. It’s hard to cut ties with one half of a couple and remain friends with the other person, so why take on all the work? You tried being The Cool Girl, it’s not working, and you don’t have to hang out with either of them to prove how open-minded and fair you are.
She may reach out, as she has in the past, to try to smooth things over, to which you can say, “I know none of this is your fault, but my friendship with [Guy] truly has come to an end, and there’s nothing to fix. I wish you well, and I don’t plan to make it weird if and when we bump into each other down the road, but I’m not going to be hanging out with [Guy] online or in real life anymore, even if that means not seeing you.”
After “more than a decade ” together (!!!!!) I presume she knows who she’s engaged to and this won’t be the first or last time he unbalances the pH in the social pool. I don’t know if she reads this website, but I’m just gonna drop this this brief, glorious tale about what can happen in when someone pesters their partner into an open relationships and hope for the best.
P.S.: Red Flag Spotting With The Captain!
- The person who complains about their existing partner at length as a strategy to get in your pants. Why do people think this is either acceptable or sexy? The “You’re cool, not like those other buzzkills who let me down” neg is a trap, it’s always been a trap, it will always be a trap.
- The person who makes unwanted sexual or romantic advances and then immediately swears you to secrecy, making their reputation somehow your responsibility from now on, and conveniently neutralizing the whisper network/early warning system about what they’re like.
- The person who gets turned down for sex and decides, well, hell, since I’m here, I might as well tell you all my problems, you can’t expect me to leave without some form of catharsis, right?
- The person who does something weird or upsetting to you, but you end the interaction reassuring and comforting them about the weird thing they did.
#ThisFuckingGuy comes in many forms, but spotting these patterns (the way today’s lovely Letter Writer did, even if she couldn’t quite define it) might save you a ton of grief.