Just got back from an exceedingly pleasant date with this chick. All good signs. Plenty of interest. Really cute petite brunette with glasses.

However, I could get a feeling of insecurity from her. She told me she was not too confident in her looks, and she’s a little uncertain about her current career too. The general vibe I got was one of someone with some self-esteem issues. Nothing too out of this world, though. Otherwise a very fun, seemingly outgoing chick.

Is a modicum of insecurity desirable? Rollo preaches a lot about competition anxiety and the importance of instilling this throughout anything long-term. While I feel like a bit of a dick saying it, I’d imagine having a chick with some shortcomings in her self-confidence can only make keeping her attention easier in anything one would wish to pursue?