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?
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.