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Dear Breakup Girl,

Hi, my friend likes this girl, I'll call her Francis, and I'll call him Julio. Well, you see, Julio likes Francis, but Francis doesn't want to go out with Julio because they are good friends. If she were a crappy friend she wouldn't even see that perspective.

Anyhow, I'm the one who is supposed to break it to him. But he has super duper low self esteem and if I break it to Julio I don't know what's going to happen... I think I should tell him in person so I can support him and maybe help him feel better if I'm there with him. Do you think that's a good idea or should I talk to him on the phone?

I feel like I'm breaking up with him. Julio's such a cool dude I'd hate to see my buddy get hurt. What should I do?

-- Estelle

Dear Estelle,

Aww! You guys are great. Normally, I warn against third-party intervention, but since this is technically not a breakup -- and since your intentions are nothing but sincere -- I'll green-light it. So yeah, in person would be good...but give Julio space to go off by himself if he wants to. And tell him you'll also facilitate when he likes someone new. (Like, maybe you?)

Love,
Breakup Girl

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