Dear Captain Awkward,
I’ve been seeing this great guy for the last 6 months. I like him a lot-he’s sweet, smart, and ridiculously generous with his time and ears.
Which makes me feel terrible about telling him to shut up about the angst he feels about his friend who’s moving away. This friend, “Allie”, works with my boyfriend, and has been working with him for the past 4 years. Unfortunately, she’s more than just his friend; he asked her out after getting to know her 2 years ago. She turned him down, but they have remained friends. When I started dating him, he told me all of this backstory, in the interests of being upfront and honest. It hasn’t really helped. In many ways, I think he still has some lingering feelings for her, from feeling hurt when she brings along a date who shares many of his interests, to wanting to drive with her cross country to help her move.
I feel like this is only being amped up because she’s leaving, but I’m tired of being supportive and listening to him going on about how he’ll miss her, and how he feels like her leaving is a bigger deal to him than to her. It grates on me to hear about his issues with his former crush, especially as I have been in a situation where I’ve dated someone with a pre-existing attachment to another girl(it didn’t end well). What is a non-bitchy way to call him out on this and help him move on?
Signed,
Insecure and Frustrated
Dear Insecure and Frustrated,
You’re one step ahead of this Letter Writer, because good news! She’s leaving! And this is also a situation that will improve with time. But it also sucks because your boyfriend and not “Allie” is the one pushing for more connection, and your frustration is understandable.
I would go for Compassionate-And-Direct:
“I know you’re really bummed about Allie leaving, and it’s bringing up a lot of complicated feelings for you. I appreciate you being so open with me about it, and I know that your intentions are good, but I also think that I’m not the right person to comfort you about this particular set of worries. Can you confide this stuff in one of your other friends, and let our time together be about us?”
I wouldn’t mention your past history in a similar situation, because that past stuff is not your boyfriend’s fault and it makes it about you instead of his behavior. (You don’t want to cloud the issue by making him feel defensive about something he can’t control and making the argument about that). There is such pressure on women never to be jealous or insecure, or if we feel that way to deny it and act cool to the end, and I’m entering a personal period of “Fuck that noise.” Your boyfriend is free to chew over his feelings for Allie and contemplate grand gestures like driving across the country with her one…last…time… and you’re free to say “I have compassion for what you are feeling and want you to process this in whatever way you need. But I need to ask you to not to do it on my time or use me as a sounding board, because hearing about it makes me feel a little insecure and crappy. I know that’s not your intention, so let’s change the subject away from Allie.”
I hope it works out and that his grieving process for what-might-have-been (a totally understandable and human thing) is over quickly.
CaptainAwkward.com 
captain: half the reason that i read these posts is to treat myself to your accompanying graphics. this one made gave me the crylaffs.
back in the olden days when i started dating theLeon he would talk about this slumpy girl. like all the damn time. i gave him a “that’s nice dear, when you want to concentrate on me again, let me know. i might still be around” speech. perhaps not the best response, but i tend to like my men focused on me (at least in my presence). i’m notaomuchandveryseriouslyamnot a fan of controlling my menfolk, but i do so enjoy clear intentions and boundaries.
Ha! A corollary to “honesty is the best policy” is “honesty does not mean total disclosure of your every waking thought.”
And having all of pop culture at my fingertips makes me drunk with power sometimes.
Some of us are just pop-culture impaired; e.g. I have no idea who those people in Question #91 are.
“So, Captain Awkward. Your pop-culture powers are useless against me. Muahahahaha!”
“You are using Bonetti’s defense against me.”
“I do not think that means what you think it means.”
“I have a relationship tip for you. Never, ever go on and on to a current girlfriend about a past girlfriend, or almost-girlfriend, or even a woman you asked out who said no and with whom you wound up settling for being friends. She does not want to hear it. Even if what you’re saying is critical rather than wistful, you make her feel like you’re more focused on the woman you’re not with than the one you are. Too much of that, and you won’t be with her, either.”
THIS.
Holy shit. I don’t go talking about exes or old crushes to anyone I’m going out with. And I wouldn’t be nearly so nice about it as Captain Awkward is (because CA is a nice person and rocks, and I am kind of the Queen of All Evil).
Yes and yes!
I spent a long time once trying to be the Cool Girlfriend (TM) until I finally realized that my boyfriend talking about other girls and how they treated him/rejected him ad nauseum was a symptom of a larger problem: he was actually a self-centered jerk who couldn’t be bothered to worry about anyone else’s feelings!
Anyway, if I had said anything this awesome to him before, I would have maybe been clued in by his inevitably insensitive overly defensive reaction.
And you know, I’ve been criticized SO MUCH by my friends for being all, “You don’t like himher? He/she knows that [behavior] bothers you but won’t try to change it? Well, DTMFA.” by my more passive friends, but while this policy of mine kept me (happily, thank you!) single for a while, it also got me this really awesome husband, who listens to me when I tell him something is on my mind. So. Be! Assertive!
Being the Cool Girlfriend (or Cool Boyfriend) is soooo overrated. I’m pretty convinced that it ultimately leads to your partner dumping you and expecting you to react with a shrug and “OK, cool”.
Yup. I think to be actually cool you’ve to to risk the Uncool.
Related: playing hard to get makes it hard for people to… actually get you! Who would’ve thought.
Here’s another pop culture reference: your boyfriend has Mentionitis, a disease leading to constant mentioning of a crushed-on person. A bad case of Mentionitis is painful to be around, and the sufferer is usually completely oblivious and thinks they’re being oh-so-subtle. I suggest you just coolly let him know you’ve noticed. “Babe, can you stop going on about Allie? I know you’re going to miss her but I’m starting to get a complex that you want to have, like, ten thousand of her babies. So anyway [change of subject]…” Crushes happen, and they’re no big deal, but you really don’t want to be listening to that.
Mentionitis! Exactly.
I love this exchange from urban dictionary:
Mentionitis: Giving away the fact one has a crush by frequently mentioning the crush object in an “innocent” context.
“Boyfriend: let’s go see Movie X
Girlfriend: Oh, Tony from the office saw that and liked it!
Boyfriend: How about pizza?
Girlfriend: sure, I saw Tony from the office having slice and am now craving one.
Girlfriend: I am leaving you for Tony from the office”
Coming to this very late, but …
A corollary to “honesty is the best policy” is “honesty does not mean total disclosure of your every waking thought.”
Yes. Yes. Yes. That works for people who don’t want to know absolutely everything, and it works for people who don’t want to tell absolutely everything.
As with all threads in which the LW never appeared in comments, I’d love to know how this worked out.