Dear Wayne and Wanda,
I have been technically single for several years, but for the last two years, I've had what you'd call a "friends with benefits" relationship with one of my guy friends. We'll call him FWB to keep it straight. FWB is good-looking and fun. Our chemistry is great. But we both know there's basically no chance of anything beyond that.
Recently, I met a new guy. We'll call him Jeff. Jeff and I met through mutual friends and hit it off right away. He messaged me on Facebook and asked me to dinner, and I went, and we had an amazing time. The night ended with a kiss ... but by the time I got home, I had a text from FWB asking if I wanted to meet up.
Now Jeff wants to go out again, FWB is still there, in the wings, available for no-strings-attached fun, and I'm completely confused about how to move forward. Do I need to tell Jeff about FWB? Or do I tell FWB about Jeff? Do I stop any interaction with FWB if I decide to go out with Jeff again? Or can I keep hooking up with FWB until I know whether things with Jeff are going to go anywhere?
The most important question to answer here is, what do you want? Do you want something casual and occasional when it suits you, or do you want to pursue an authentic full-time relationship? Neither answer is wrong or right, but you do have to choose at some point, and sooner than later, for everyone's sake.
Simply put, no, you can't pursue a relationship with Jeff while still shagging FWB. After all, how would you feel months down the road if you learned that during those first few shiny-new and sparkly dates with Jeff, he was still sleeping with his neighbor or ex? There's something to be said for a clean slate and if you really want a boyfriend, a partner, an honest-to-goodness day-to-day relationship, then you need to leave all baggage at the gate and start fresh.
But you seem pretty content with FWB while stumbling into this connection with Jeff nearly by accident. Maybe you aren't ready for commitment, or to give the time that a relationship requires. In that case, politely decline Jeff's second date invite and free him up to find a female who is relationship-minded.
One of the great, ahem, benefits of a great FWB relationship is that participants can end it at any time for any reason. Exhausted by all those late-night booty calls/texts? It's a wrap! Would rather watch the 2013 MLB Home Run Derby than respond to a benefits request? See ya later! Struggling with the ethical and emotional implications of simultaneous dalliances with multiple men? Probably time to call it a day.
One of the great benefits of being single is that you don't really owe anyone anything other. It's perfectly fine for a single person to go on a dinner date with a new interest and share dessert with an old flame later -- just be sure to put your phone on vibrate in case your booty calls start arriving during appetizers.
But you're already struggling with the "technically single" part. And if things continue to progress with Jeff over that second date -- and all indications are that they will -- it's only fair that you decide what you're doing and, like Wanda said, what you want. Don't talk to them about one another. Don't drag them through your decision drama. Be honest with yourself, make up your mind and commit to it.
• 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.