Shy Thirty-something Needs to Do Something

Dear Harlan,

I am a single 35-year-old woman who has not dated very much -- in large part, I believe, due to my shyness. I have had a few short-lived relationships but have never been in a long-term relationship. I am curious to know, from your perspective (as a guy), if men would see my lack of relationship experience at my age as a red flag.

Dateless and Doubtful

Dear Dateless and Doubtful,

Personally, I prefer a woman who knows what she wants and isn't afraid to express it. This way, I know where I stand. But still, you're perfectly desirable. A lot of men prefer shy women (a lot of guys are shy). Some of them love shy women because it's a comfortable fit; others love shy women because they're more easily manipulated and exploited. A women who doesn't have much confidence is easily manipulated and exploited (that's the scary part). More important than how men feel about you is how you feel about yourself. The moment you know you're hot and desirable and are a hidden treasure flying under the radar is the moment men will see it. Shyness is only a red flag if you're stuck hiding behind it.