Dear Wayne and Wanda,
With Valentine's Day upon us, I'm questioning my relationship and needing some advice. I've been dating my current man since early December. We are both in our late 20s. We have each met a couple of each other's family members, but not all of them. We've met some of each other's friends, but not all of them. We aren't friends on Facebook and we haven't really talked about what our status is. So I guess while we've made progress, I'm not sure where this is going. But I want it to go somewhere.
When we first met (at a bar, through friends) we saw each other a few times a week. Lately it's about once a week. The last time we met up, I jokingly told him I was worried he was losing interest, and he kissed me and said he's "crazy" about me and to relax.
I've been relaxing for two months! For Valentine's Day, we are going to a nice restaurant downtown -- by far the nicest place he has taken me. I am totally excited and think this could be the beginning of the next phase of our relationship. So my question is: is it OK to bring this up at dinner? In a public place? I mean, Valentine's Day seems the perfect time to do that. Thoughts?
Wanda says: Ahh, the DTR -- that's the "defining the relationship" talk for those of you who don't read chick lit, watch rom-coms, or haven't been single since 2002. It's a make-or-break conversation, a "do not pass Go" or "move on to the winners' circle" event. Many avoid it because they aren't ready for the finality of the outcome either way, and would rather wallow in the non-relationship gray area than force the question and get dumped entirely. In other words, they'd rather have something than nothing -- or everything.
I have a long-touted mantra: as long as you're with someone who isn't giving you what you want, you can't be with someone who will. There's a "but" clause to this: maybe that person you are with will give you what you want, but you have to ask. But if you ask, they might say no. Super scary. It's like one of those "pick-a-path" novels I read as a kid.
You're ready for The Talk. Is Valentine's Day the right time? Debatable. It's a high-stakes holiday with a ton of pressure on the man to deliver romance. You might be better off riding out the night and staying super alert to his words and actions. Is he just stoked to be around a cute, fun chick, or is he sparking and vibing on you? Be aware and move forward from there.
Wayne says: Wanda, I think you meant "Choose Your Own Adventure" books. Those were a lot of fun -- so much riding on each turn of the page. P.S. Never pick the dimly lit cave! Never!
Miss DTR-ready is definitely at the end of a chapter with a big decision to make: "To start the DTR on the big date and potentially ruin the night or secure your relationship, turn to Page 27" or "To enjoy a fancy dinner and Champagne and avoid potential relationship meltdown on Valentine's Day, turn to Page 34."
Honestly, there are fewer words men cringe at more than "We need to talk." Doesn't matter if they're coming from a boss, a parent or a romantic interest. Most of us instantly freeze up or go on defense. He's ready to wine and dine you -- there is a 10 percent chance that he will positively respond to hearing this sentence. Sure, maybe it was his plan all along to make it official with you on Valentine's -- how romantic! More than likely, he'll squirm. There's even a chance he'll say, "Check, please!" Is this the lasting Valentine's memory you want?
You've been dating for three months, you've hung out with family, and you're his Valentine's date -- sounds like your status is unofficially "in a relationship." Trying to make it official on V-day is a bad call. If defining the relationship is truly eating at you, have the conversation before the date. That way, you can "Enjoy the night as a couple on Page 92" or "Spend the night with your girlfriends eating ice cream and trashing men on Page 103."
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