Dear Dr. Lovemonkey,
I’m a longtime reader, and first-time writer. I was pleased to see your recent response to Annie, the waitress who complained about getting hit upon by customers. As a self-respecting gentleman, it has been a set understanding not to cross the personal line with those in the service industry. Ladies, particularly the attractive ones, put up with far too much unwanted attention every day, as Annie points out, to need any more from me. Furthermore, since their very wage is dependent on making others feel comfortable and welcome, it is unfair to interpret their friendliness as anything more than polite business.
Herein lies my question: if I am personally interested in a waitress, when — if ever — is it appropriate to cross that line? How does one go about this without being lumped in with the troglodytes who Annie finds so annoying?
_Don’t Date the Help
Dear Don’t,
I get the impression that you are a co-worker of your prospective interest, but perhaps I’m mistaken. Regardless, proffering a friendly invitation for coffee or some other innocuous situation might be the best way to handle this. If she’s amenable, you can slowly reveal how you are interested in being a bit more amorous. If you are thoughtful and sensitive about your approach, you might find that your interest is also interested. It’s all about context. The customer/service personnel relationship has to be severed for this to be successful.
Hairy situation
Dear Dr. Lovemonkey,
My girlfriend recently got a haircut and she keeps asking me how I like it. Even though I don’t “dislike” it, it is startlingly shorter than how she used to wear her hair. I’m straining to say the right thing here, but I’m still getting used to it. Should I lie and tell her that I really love it, or should I continue to say that I’m still getting used to it?
_Bobby
Dear Bobby,
Lie like a rug. Tell her that it’s the greatest haircut of all time, and that you are considering getting a matching ’do just to show her how much you like it. Dr. Lovemonkey understands how important hairstyles are to almost everyone. I know this because I have no hair on my head.
The important thing here is how she likes her cut. Like you, she is still likely “getting used to it,” and is therefore a little unsure of what she and her stylist have done. Although telling her you’re still getting used to it may seem logical, this isn’t what she wants to hear about her hair. Try point out all the pluses of her new hairdo. Perhaps you can see more of her face, and because you love her face, this is a plus. People like their appearances to be validated by others, especially those closest to them.
Because of my baldness, Dr. Lovemonkey is as lost as you seem to be on this question. Maybe some of my readers have suggestions about what to do under these circumstances. Please feel free, dear readers, to enlighten Bobby and the Doctor.
Third party
Dear Dr. Lovemonkey,
I’ve been married for almost five years. While my wife and I have a good sexual relationship, I’m thinking about hiring a male stripper, because I think this might enhance the sexual dynamic between us. There are times when I’ve watched a stripper and then come home and had really good sex with my wife. She seems to be behind this idea. What do you think?
_Heating Up
Dear Heating,
If you both like the idea, then go for it. Just don’t get too “behind it,” if you know what I mean.
Email the author
Dr. Lovemonkey: rudycheeks@prodigy.net
