[April Masini, your AskApril]

First of all, don’t worry about rejection too much. It’s part of the bigger picture, and the secret is that if someone rejects you, they’re saving you from wasting time on Ms. Wrong. So try and understand rejection happens. That said — this may not be a rejection! 😉

Second of all, flirting is very important in dating. It makes women feel good about themselves because they know that you find them attractive. It also changes the nature of the relationship from platonic to possibly romantic.

Thirdly and most importantly, because this woman is a family friend, there’s probably a weird feeling of incest because your family is friends with her family. The best way to get rid of that weirdness is not to slide into a relationship, but instead, to formally ask her out on a date. That way there’s no mistaking your intention as something creepy.

As for being handicapped, I’m not sure that that has anything to do with your being charming, smart and sexy! Women love men who are successful and powerful and everybody’s got something. 😉 Let me know if that helps — or if you want to be more specific and I can respond in kind.

Let me know how it goes — and please follow me @AskAprilcom on Twitter as well as on Facebook at this link: [url][/url]. 😀