Dear Harlan,

I have a good friend who has always struggled with girls. This one girl has really come on to him. She posts on his Facebook wall (usually pictures of herself, which I find odd) and asks why he didn’t text in a couple days. It’s clear, at least to me and in the eyes of others, that she really likes him. However, a friend of his really likes her too. I keep telling him that if she isn’t into that other guy, then it sucks to be him. I’ve been where that friend is, and yes, it sucks, but he will get over it.

However, he keeps saying “we will see” and “I don’t know if I can date her, because of my friend.” What do I need to tell him so he will take the shot? He’s never had a girlfriend, so I feel like this may have something to do with his inexperience. Obviously, I can’t make them date. But he likes her, yet he is so worried about hurting another dude’s feelings. I feel like he needs to be a little selfish here. Girls don’t usually chase the guy. This is a unique position, and it’s a good one for him because he doesn’t often approach girls. What can I do to get him to pull the trigger?


Dear Wingman,

Don’t expect him to pull anything, at least not the trigger. Here’s a better plan — let the girl who wants to date him do the pulling. She’s a strong woman who knows what she wants and isn’t afraid to get it. Make your friend an easier target for her. Encourage your friend to hang out in a group setting and ask him to invite her. Offer to help make it happen. Or bump into the girl your friend finds attractive. If it feels right, mention that your friend might be interested, but doesn’t want to hurt the other guy’s feelings. This will give her even more motivation to go after your friend. Your job isn’t to force your friend to do anything that makes him uncomfortable. Force him into situations where women who want him can help him get comfortable with the uncomfortable. In the meantime, live your life as an example for your friend. Being around your self-confidence and support is immeasurable (in a good way).

Dear Harlan,

I value myself as a strong woman with high standards. How do you know if you are too good for a guy you are dating?

Too Good

Dear Too Good,

The Rule: When you have to ask yourself if you’re too good for a guy, he’s not good enough. But here’s the catch — if you ask this question over and over again with every single man you’re dating, you might be the problem. Some women will call themselves picky and pick over every man.

What these women can’t see is that they’re not looking for someone “good enough,” but rather someone better than themselves to help prop them up. If you find that you can never find a good man, make sure you are at your very best. If you need help getting better or finding someone better, find a therapist or psychologist to help guide you. You need to have some pros in your corner.

Harlan is author of “Getting Naked: Five Steps to Finding the Love of Your Life (While Fully Clothed and Totally Sober)” (St. Martin’s Press). Write Harlan at [email protected] or visit online: All letters submitted become property of the author.

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