Got a relationship question you want to ask, or a situation you want thoughts and advice on? Email me at somedude.harvardfml@gmail.com, and watch this space for my answer! Today, I’m going to talk about overcoming shyness. If you are a shy guy, what can you do to overcome that reluctance? And if you’re a girl interested in (or already in a relationship with) a shy guy, how do you deal with it?

Friends with Detriments by xkcd.

For afflicted guys: there are basically two kinds of you: the kind that will hang out with a girl you’re interested in, doing her favors in the (possibly subconscious) hope that friendship will eventually turn romantic; and the kind that is too shy to do anything other than admire from a distance, wondering if the object of your affections even knows you exist. And there’s a lot of overlap between them.

I used to be one of these guys. I was not motivated to change myself, either, because I’ve always been both relentlessly optimistic and very good at accepting defeat. I grew some confidence accidentally, by reading a self-help book on smalltalk, without any agenda in mind, and applying it to non-romantic things in my life. Grasping social success for the first time gave me confidence, which made me more willing to take risks. That’s ultimately the goal, because being more willing to take those ordinary social risks helps make them less risky. What shy guys are afraid of usually isn’t actually rejection itself, but the self-imposed shame and embarrassment of rejection, and overcoming that makes you come across as more attractive and therefore less likely to be rejected in the first place.

Specific techniques can give you confidence by knowing that you’re doing something right, and seeing the positive results builds a virtuous cycle of social confidence. I’ve written about these techniques before so I won’t reproduce them at length here; try them!

For girls interested in shy guys: do not wait for the guy to take the lead. If you’re interested, express interest. Do not be subtle; shy guys will over-analyze subtlety and become paralyzed not knowing what you meant. Be overt. For instance, walk up to him, give him a lingering kiss on the cheek, and tell him to get coffee with you. It’s bold, it’s unambiguous, and still romantic!

Don’t expect the shyness to go away after your first interaction – you will probably have to continue to make important first moves. Once you’ve done something first, he’ll be less shy about the same thing on subsequent occasions (asking out, making out, having sex). Once you have a budding relationship you can talk to him openly and honestly about his being able to take the lead – if he hears it explicitly from you, and knows in advance the sort of circumstances under which you’ll shut him down, he’ll feel more confident.

Stay tuned next time for Overcoming Shyness for women!

Special thanks to Leil Lowndes, HRG&SP, and Ben Nelson’s address book. Email Some Dude at somedude.harvardfml@gmail.com.