Dear Wayne and Wanda,
I started dating a new guy recently. We've been taking it slow, but he hasn't always taken that approach. He's hooked up with a lot of women.
At first I thought I was OK with that, but we're always bumping into someone he knows when we're out. At some point later in the night when it's just the two of us, he'll admit that the person we ran into was someone he's hooked up with. And even when he doesn't mention it afterward, I find myself wondering but too embarrassed to ask.
Sometimes I worry that I'm being a prude, but I don't think so, right? It's natural to be a little uncomfortable with this, isn't it?
- Slow and Steady
Wayne: Perfectly natural. We're talking about sex here, one of the most uncomfortable topics to discuss in any setting. And even though you're in the just-getting-to-know-you phase with this guy, you're quickly entering the TMI zone with him as well -- also just a little bit awkward.
While awkward and uncomfortable might come with the sex conversation, he isn't making it any easier by spelling out his sexual exploits before you've even had sexual exploits of your own! I wonder why? Is he trying to impress you? Let you know he's an incredibly desired man? Pressure you to speed things up? Feel good about himself? Whatever the case, it isn't working.
Heck, I wonder if his tales are even true. Us guys aren't exactly the best accountants when it comes to our sexual histories. That legend of guys always adding two or three to their tally and women subtracting two or three from theirs? Totally true.
While he has his reasons for bragging about his shagging, you have good reasons for taking things slow with him. Don't let his boasting about his past take you to an insecure place or pressure you into speeding up your pace. In fact, you should be real with him and tell him that all of his talk about sex with other women is a big turnoff for you. That ought to shut him up.
Wanda: It's definitely natural to feel discomfort. If you were high-fiving him and egging him on for details, that would land you solidly in the Friend Zone. The best thing you can do is tell him how you feel. Let him know that you enjoy spending time with him, and when you're sharing that time together, you'd rather focus on the here-and-now and the possibilities of the future, not on past conquests and post-mortems on relationships gone wrong.
But let's cut the guy a little slack too. Anchorage is a small town, and exes are everywhere -- at the gym, at work, in the produce section at Carrs and out at the bars and restaurants. It's only natural that as we go about our daily lives, we will run into former flames.
What's the protocol when you encounter an ex with a new partner on your arm? It sounds like your man is taking the route of total disclosure. The alternatives would be to say nothing and pretend he doesn't know the girl or only selectively clue you in on the full nature of his involvement with these women you randomly come across. If you think about it, either of those options are inherently dishonest. It sounds like he's trying to be a stand-up guy and not hide anything from you.
The only problem is that there's such a thing as too much information. Thank him for his apparent willingness to share, but let him know you're fine postponing those talks until much further down the road, and for now, you just want to focus on each other.
And as far as feeling like a prude or being worried about how you'll stand up against this backlog of lovers, take comfort in the fact that he's with you now. There is such a thing as quality over quantity.
• Wanda is a wise person who has loved, lost and believes in retail therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at firstname.lastname@example.org.