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“But there are also some who try very hard only to get rejected over and over again from even first dates.” He might be lacking in confidence because the last woman (or women) he went after gave him the cold shoulder—or worse.

“I think we spend a lot of wasted time trying to be someone the woman wants,” Charles says, “And lose confidence when it doesn't work.”“Most guys struggle to communicate (worse now with media/texting),” Mark says.

Well, from what I can tell, that typically means he is acting weakly, and he needs to do the opposite. When we’re talking about romantic relationships, that means be assertive. If you like the way things are going, commit to her.

If you’re on the fence, make a decision one way or the other. While those simple ideas are all well and good—and appealing, as we men like to think of ourselves as simple creatures—that doesn’t mean there’s a simple answer.

And, to make the matter even less simple, it might be a combination of things. I took your questions to real men near and far and asked them point-blank: Do men need to man up? “But some men may be struggling internally with various issues that prevent them from asking a classy dame out on a date.” While it may be a surprise to some women, I’ve seen firsthand how other factors can negatively affect our confidence with women, namely professional frustration.

For me, I would have been happy to pursue a woman if I knew she wouldn’t get hung up on my career advancement (or lack thereof) at the time.“Yes, men can do a better job,” my buddy Mark says.

It’s one of the most common complaints in the dating landscape: dealing with mixed signals from a potential partner.

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The conversation got really weird, in fact: she started asking me about my sexual exploits post-breakup, and telling me about hers, in richness of detail. Thing is, I took that as a possible sign that she was down for some casual sex and started subtly flirting with her.

We decided to meet in the near future halfway through the conversation, but she picked up on my hints and said she wasn’t interested.

She even said she was sorry if she ever made me feel like I had done something wrong; the problem, she said, was that she felt that was not the sort of relationship she wanted at the time.

The night went on, and I was reminded of how much we had in common, Doc.