Dear Dr. Lovemonkey,
After dating for seven years, I decided to propose to my girlfriend. We were engaged for a year, but she called it off three weeks before the wedding. She said she just wasn’t ready to get married. We tried counseling for a few months, but things fell apart a few months later. Now I’m single and I’m worried that I’ve lost it. I used to be sort of a free spirit and an artist; that’s one of the reasons why my girlfriend fell in love with me. Now I work a desk job. As I’m now approaching 30, I feel a little unhip, and I think I’ve forgotten how to date. Got any tips?
_Unhip Deskmonkey
Dear Unhip,
If you two were together for seven years, engaged for another year, and she then says she isn’t ready to get married, believe me, she isn’t ready. More specifically, she’s not ready to get married to you. It is best that you both move on. Having a job in the 9-to-5 world does not make you unhip. You are evolving, and that evolution will continue for the rest of your life — the same as it does for anyone. You need to find someone who wants to go on that journey with you, and someone whose journey you want to be on. That person should be able to grasp your essence and vice versa. Neither of you should be stuck in one narrow persona. You can’t forget how to date, because there is no single way to date. Have fun, be open, and meet people.
Take the plunge
Dear Dr. Lovemonkey,
I am in my 50s and recently fell in love with a widower my age. Because I am embarrassed, I have been making excuses for not having sex with him. I’ve had sex only once. It was such a bad experience that I quit dating for 20 years and concentrated on my career. I assume I must be in love because I’ve had dozens of crushes, but never this kind of emotional intensity. Now I’m afraid that my inexperience will turn him off, and I’m considering saying that I don’t want to see him again. I read The Joy of Sex but this book seems to assume that you know what you’re doing. Can you recommend any good instruction books? Should I tell him about my inexperience?
_Unsure
Dear Unsure,
I would certainly reveal your story and tell all about your inexperience. Explain why you are telling him this in a way that you find embarrassing and difficult — because you have such strong feelings about him. If he has strong feelings for you, he should be willing to find a way to work things out and make you comfortable. Whatever the sexual experiences to come, they can’t be worse than the your initial one, so know that things can only improve. Nothing will happen unless you take some risks.
