I told my friend about it casually, and she didn't seem to care. But a week or so ago, she told me she'd go out with him if he had more free time. I'm scared to tell him I like him because I don't want her to get mad at me. But I really like him. I feel like if she's my friend, she'll understand and even if she doesn't like it, she'll at least tell me in a nice way and not get mad. But at the same time, I feel like I should respect her past, and leave him alone.
--Lonely In-love

Dear Lonely In Love:
Kudos for being considerate and thinking about how your friend might feel about you and her ex. That ability to place others feelings above your own is a definite sign of maturity.
You don't say how that relationship ended, but clearly it ran its course. Either she lost interest in him or vice-versa. In any case, it wasn't meant to be. Eighteen months have passed. To me, that is ample time for you to wait until you date a friend's ex. Now if it was three weeks, I'd be writing different advice, but that's not the case. I say go for it. Join the hunt and pursue your catch.
Of course, your friend will be jealous and upset about you and John together. But what can she say? Stay away from him? What if she dated six guys in the last four years? Are you to avoid them all? There may be only six decent guys in town.
To avoid a problem with your friend, tell her that you are interested in John and want to see where it goes. The key word is "tell." Don't ask your friend for permission to date John. Just tell her you respect her and your friendship and want her to hear it from you, rather than from someone else. It's like a guy asking for a father's blessing to marry his daughter. He isn't really asking "permission" to marry his daughter, but simply being respectful by informing his girlfriend's father before he asks for his daughter's hand in marriage.
Your friend should respond positively to this show of friendship. If she freaks, tell her that this is not negotiable. Stand your ground. Be strong and let her come to the conclusion that John likes you now.
Her feelings will be hurt. Unfortunately, you are not the person to console her -- even though you may want to. She might also bad mouth you, but don't take it personally. She's just venting her hurt feelings. In time she'll come around, especially when she finds another guy. She'll also realize what a good friend you really are, and what a good couple you and John make.

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