Dear Wayne and Wanda,
I've been on a few dates with this guy. I'll call him Bob. Bob is super nice, very sweet, very stable,and we have had a good time together. But it just isn't quite what I'm looking for. While we were hanging out, I met Bob's best friend, Tim. Tim is really different from Bob. He's more of a mystery. I find myself thinking about him -- thinking about him a lot more than I was thinking of Bob. So I told Bob I just don't think he's the right guy for me. He is super bummed and asked me to reconsider, but I don't think I will change my mind. The thing is, I think I really like Tim and I know Tim likes me because he texted me and said if things aren't working out with Bob, we should hang out.
I don't know what to do. I really think Tim is cool and I would love to hang out with him. But Bob is such a nice guy and I know I already hurt his feelings. It isn't like Bob and I are close though. I mean, I only went out with him a few times. Wouldn't it be stupid to turn down a chance with Tim to spare the feelings of someone I hardly even know? I need advice. Thanks!
First things first. Tie up your loose ends. It sounds like things with Bob aren't entirely over. He has asked you to reconsider the break-up. Give the poor guy some closure, especially before you start hooking up with his best friend. Tell him face-to-face, or at least in a phone call, that you've thought about it and in the end you just know you guys aren't meant to be. These conversations are never fun or easy but in the end, it's about respecting the fact that the other person has invested time in this too and deserves a little closure.
Once that's done, you have a choice to make: whether or not to pursue Tim. If you ask me, he kind of sounds like a dirt bag, creeping around behind his buddy's back, texting you before the relationship dust with Bob has even settled. If he treats his friends this way, how do you think he'll treat a girlfriend?
Furthermore, do you even want to be someone's girlfriend right now? What are you really looking for? It doesn't sound like you're completely ready to be in a committed relationship. If you're finding a nice, stable guy like Bob to be boring and an opportunistic flirt like Tim to be more compelling, maybe you're better off staying single and playing the field for now.
Wow, who needs frenemies when you've got besties like Tim?
Making inroads with someone who is currently involved with one of your good friends is a grave violation of friend code. And most friend groups (male and female) seriously frown on friends getting involved with friends' exes. It's that kind of social circle incest that creates awkwardness, makes friends choose sides, or simply destroys friendships entirely. Is it worth it? Really?
Hey, dating is an adventure -- sometimes it's awesome, sometimes it's tragic, sometimes it's bittersweet. And sure, it's tough finding interesting people you have chemistry with. But let's be realistic: How great can Tim really be? If he's cold-blooded enough to sneak behind his best friend's back to holler at a girl, I don't think it's a stretch to think that one day he could be trying to hook up with one of your friends behind your back.
I say chalk this up to bad boys and bad timing. Dump Bob, ignore Tim and wait for the next group of boys to come along.
• Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at firstname.lastname@example.org.