Four years of mixed messages

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Dear Guys,

So, here’s the deal. There’s a guy I’ve known for years, since I was 22, and I’m now 33. He was married the whole time I knew him until about 4 and half years ago. I’d always liked him, but he was married so it was just one of those “all the good ones are taken sort of thing.” Anyway, he got divorced because she left him for another man and did I mention that he’d told me they slept in separate rooms for years?

Anyway, we ended up making out one night after an event-after his divorce had been final for a few months. He made the first move, but he said he didn’t think we should sleep together. The next day at the conference he said listen I’m not ready for a relationship. I said okay, let’s just be friends.

We went out a few times after that. Once golfing, once for drinks, and once he came over to watch a football game. We almost had sex one of those times, but again he pulled back and said he didn’t think it was a good idea.

A few months later after another event we made out again. Then nothing. The following year after the same event it happened again and still no sex. This year same thing. I finally called him on it and said this has been going on for 4 years, fish or cut bait (basically). This forced us to have a long talk that was way overdue. During that  long talk he said he loved it when earlier in the evening we’d sat and watched the basketball game and I was leaning on him with my head on his shoulder. He said that was so nice. I want more of that.

He said it really isn’t that he doesn’t want to sleep with me, but he’s afraid it will be awkward later and could ruin things. He went on to tell me in pretty explicit and anatomically correct vocabulary exactly what he’d like to have happen. Then he said we should maybe try hanging out and see what happens. He said I want to sleep with you, but I don’t want to do it like this. I said so you want to go out on a date and he said yeah. I said okay, call me in the next two weeks and ask me out. If you do I’ll say yes.

He hasn’t called. Seriously? My friends say I just need to take the lead with him because he has a bruised ego from his first wife and he’s afraid to sleep with me and afraid I’ll reject him. Help please, I’m not sure what to do next.



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Dear Laine,

Thanks for your question.

Your friends may be right. He could very well feel vulnerable, especially with the way his marriage ended. It might be harder for him to trust people now in general. And it is possible he could be unsure how a new woman might evaluate him, especially as a sexual partner. (Yes, this is how guys are.)

However, it could just be that he’s not ready to get into another relationship. It’s hard to say how long it takes people to recover from a failed marriage or relationship, but in his case it sounds like it’s taking a while.

It also sounds like he’d like to take your relationship from the casual sphere- of occasionally “hooking up”- to a more formal courting situation. That way he can take his time and move slowly if he needs to. This will also help him get to know you as a potential partner. It’s hard to do that when you just hang out with someone after various events but don’t have the day to day communication and closeness that should accompany that.

Where we disagree with your friends is your role here. We still think you need to leave the ball in his court, even after he didn’t call you. (Which does bother us by the way.) Considering the circumstances we think you should give him one more chance.  Tell him again that you’re interested and open to having him ask you out on an actual date. If he still doesn’t take the initiative after getting the green light from you a second time, we think it’s time to move on. Don’t put up with game playing. That’s something that doesn’t change over the course of a relationship. And guys in general should still be the ones making the first move,  especially when the woman-you in this case-is making it easy.

Best of luck,


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