Finally! Some good weather is coming our way…which means some of our staff members are beginning to feel the effects of Spring allergies. Aaaahh-choo!

Anyhoo, here’s this week’s question from Sam from Yonkers, who cornered us at a party and asked our advice about the following: “I want to ask out my friend’s ex-girlfriend. They’ve been broken up for over a year and I’ve been in touch with her a lot. Even when they were dating, we hung out without my friend, which was fine with him then. Is that okay to do?”

First, we recommend you read one of our recent posts about the possibility of ruining a friendship in exchange for a relationship, which has similar pieces of advice: take a good look at your friendship and consider the fact that you’ll possibly lose him for good if you attempt to court your friend’s ex. Sure, it’s been over a year. But feelings don’t exactly fade even after 365 days.

So here’s a different angle on a strategy: Sam, you mentioned you were in touch with the ex and were friendly with her. We’re thinking you should call her up and say that you want to hang out. Make it casual – a coffee at your local cafe, a quick bite, or a run around the Reservoir. If you have fun or if you feel that she’s thinking the same thing, let her take the reins. This reminds us of our very first post, where we discussed the mere exposure effect, which applies to what you’d like to happen here.

Let’s face it, ex-gf’s know the basic rules about dating friends of their ex-bf’s. Sam, if she makes the decision to take the plunge, some of the pressure comes off you in some ways. Maybe your friend feels better if both of you come to him and explain the situation. Or you see if things really work before you take that next step and tell your friend the situation.

And let’s say she doesn’t start crushing on you. Then no harm, no foul. You don’t have to tell your friend that you’re pursuing his ex. There’s really no sneaking around going on – let’s say she tells him you went running with her: you just say that you’re friendly with her, which isn’t a big deal.

This is all contingent upon how you want to deal with your friendship. We’ll warn you once more that guys don’t exactly react well to their friends dating their exes, depending on how they broke up or what’s transpired after their relationship. Good luck with this one, Sam. It’s tricky.

Askmen.com breaks it down the situation for you in great detail. How to Do Things has five ways to reduce the awkwardness.