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.

Too Much Time With Ex is Too Much To Look Past

Dear Harlan,

I am having trouble dealing with the amount of time my current partner spends with her ex. Although they had not been dating for the past six months, she slept with him on occasion. She often calls him for rides to places, goes out to eat with him and routinely cancels dinner plans. He is constantly telling her how lonely he is and how much he misses her. My anxiety over the situation reached a boiling point when her aunt and cousin were in town and she blew me off to have dinner with him and her family. I have expressed my feelings to her, and she says that she is not going to stop seeing him. I don't want to have to ask her to not see him. This would make me look like a jealous person and possibly drive her and her ex closer together. I like her, but I don't know how much I can handle.

Questioning Questionable Partner

Dear Questioning,

If you knew you could date other woman, would you date this one? The answer is NO WAY! It's absurd that your girlfriend blows you off to be with her ex. It's even more absurd that you put up with it. Millions of partners tolerate the intolerable because they don't think they can do better. Well, you can do a lot better. If you do become her new ex, maybe she'll find the time to be with you. She seems to like her exes.