What should I do if one of my friends is hooking up with my ex? —Derek, senior

Matt: First, think back on you and your friend’s relationship. Is most of it just superficial chatter and getting drunk at parties together? If no substance is present, you should have fewer qualms about your friend’s interest in your ex.

If he really is a good friend and someone who matters in your life, think about if you want to salvage the friendship. Confronting him could cause more problems than a friend’s worth, and confronting him could cause your ex to become involved in your life again, in turn forcing you to confront old feelings.

If you decide your friend is no longer worth it, have some harmless fun. Casually mention to your friend that your feelings for your ex are coming back, and take note of his reaction. Talk about how much you miss the sex and throw out lines like, “You can’t even imagine what the sex was like.” See if he freaks out or becomes nervous. As harsh and unwarranted as this may be, it could actually save your friendship.

He may confess to you what’s been going on with your ex, and admit he was too hesitant to talk to you about it. And then you two would talk about it, like friends would. He may have slept with your ex, but at the end of the day, an ex is still an ex. Whom your ex sleeps with really shouldn’t concern you anymore, even if it is one of your friends.

Fran: Judge the situation based on how long you dated your ex, not how long or how well you have known your friend. If you were in a serious relationship with your ex and all your friends knew how devastated you were when you two broke up, it’s not okay for your friend to date your ex—ever. But if your relationship was short-lived and the breakup was mutual, you should probably get over it. Your friend or your ex should have told you about the relationship right away, though.

You have to remember this is simply idealistic advice. Two years ago, one of my best friends slept with my ex-boyfriend on my birthday. At my apartment. She thought I wouldn’t mind because I had been dating my current boyfriend for almost two years at that point. She also assumed the intense feelings I had for my ex-boyfriend were long forgotten because both he and my current boyfriend attended my birthday party that night. What she didn’t take into consideration was that my ex and I had dated for two years, as well. He gave me a promise ring after he graduated and moved to Lawrence when I was still in high school an hour and a half away. She listened to me cry on the phone for hours every day the first month after we broke up. She clearly misjudged the way I would react to finding out they had slept together. I have not talked to her since that happened, and that was almost a year and a half ago.

What you do is up to you in this situation, but I wouldn’t blame you if you cut your friend out of your life. Although it’s not the mature thing to do, I can’t say I wouldn’t do the same thing, even if I had only dated my ex for a few months.

When is a good time to retrieve your belongings from an ex? —James, junior

Matt: Get your belongings ASAP, right now, without hesitation, PDQ. I don’t even know what you’re doing reading this response, James. You should be on your way to get your stuff.

Do not wait a month. Or even a week. That month or week of you looking at your ex’s stuff causes you to reminisce about your relationship. Stuff really is just stuff, and having it sit around causes you to think about the person—your ex—who owns that stuff. If the relationship has no hope of being salvaged, the “out of sight, out of mind” approach is the best way to go.

If you’re just not ready to do this, have a mutual friend do it. There’s no need for an awkward moment when a friend asks you where you got, for example, a shirt you are wearing, and having to answer, “It was my ex’s.” We all know what’s going through that friend’s head: You must not be over your ex. And if you really are over your ex, you should have no problem giving back what’s not yours.

Fran: If you don’t really want the relationship to be over, don’t initiate giving back personal items just yet.

One of my friends, we’ll call him David, broke up with his girlfriend because he was angry with her, yet he intended to get back together with her when he calmed down.

In the meantime, she decided to drop by his place to get her stuff back because she thought it was completely over. David was not at home when she stopped by, but his roommate Ted was. Ted did not understand the situation and thought it would be easier if she retrieved her stuff while my friend was not at home, so he broke into my friend’s locked room with a butter knife so David’s ex could get her stuff. To make a long story short, my friend did not notice that his ex had taken her belongings until several days later. By that time she had already done the breakup ritual and she did not want to go through the pain and hassle of getting back together. To this day, my friend still names Ted as the reason he and his ex ultimately ended their relationship.

The moral of the story is: Do not exchange items with an ex, do not let your friends or your ex know you are thinking about exchanging items, unless you plan on following through with the breakup. Once you put those items in a box and give them back, I doubt you will ever see them again. Unless you know Derek’s friend. Then you might be seeing those items again really soon, just not the way you thought you would.