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Making a Smooth First Move

How to approach women, plus exchanging gifts and tipping condo valets.

Miss Conduct
(Illustration / Nathalie Dion)
 An Affair to Share? (9/16/07)

How do I approach or introduce myself to a beautiful young woman who parks her car in my neighborhood (where I also work) every day? Your thoughts would be appreciated.
S.K. in Roxbury

Be straightforward. You know more or less where she's going to be every morning, right? So be there yourself some day, enjoying a coffee or flipping through the newspaper – and say, "Hi!" Then you can make some bit of small talk, asking her about her car or the weather or something. Whatever you say doesn't have to be witty or insightful. It just needs to communicate two things: that you would like to get to know her, and that it is truly and completely OK if she does not want to get to know you.

I can't stress that last point enough. The ultimate key to succeeding with women is to make it clear that you can take being turned down. Some guys sort of get this but think it's about coming off as cool and detached or playing hard to get. That's not quite it. It isn't that women are driven mad by the unattainable; it's that nearly every woman alive has had an unpleasant encounter with a man who expressed romantic interest and then turned unpleasant when she didn't respond as he wanted. Maybe it was a construction worker who followed up "Hey, baby" with a string of obscenities when she walked by without a smile. Maybe it was a professional at a conference who was full of friendly interest until he found out she had a boyfriend, at which point he suddenly wanted to network elsewhere. Nearly every woman has had some version of this experience, and we hate it. So don't be that guy. Be the other guy, the guy who's cool and low-pressure and treats women like people, so that even if she's not interested, she'll think, "You know, he's not for me, but my friend Andrea would be all over this dude."

Don't give in to the temptation for romantic gestures. Save the rose and sonnets under the windshield wiper for after you've been going out awhile (when they'll have greater impact, anyway). As a first move, such gestures work beautifully in romantic comedies but in real life can leave a woman wondering if she's got Cyrano or a stalker on her hands.

My boss gave me an expensive handbag as an inducement to stay with her company. I thanked her sincerely and have stayed with her company (not because of the gift, for sure). The bag came with a gift receipt and, as it was not my style at all, I traded it for two other bags. My friend thinks I shouldn't have exchanged the gift. I do intend to show my choices to the boss, with thanks again, and I don't think I did anything incorrect. What do you think?
L.C. in Boston

Opinions differ on the appropriateness of exchanging gifts (which means I'll get lots of letters from people on both sides insisting that opinions do not differ; it is simply that they are right and everyone else is wrong). When such differences exist, it's often best to err on the side of propriety – especially when dealing with your boss. This is probably what your friend is thinking.

However, you know your boss, and your friend does not. My feeling is that if your instincts were right to keep the job, they were also right to exchange the bag. If your boss is driven by reason rather than emotion or ego, wants her employees to be happy, and appreciates initiative, then she won't mind that you exchanged the handbag for one that suited you better. And if she isn't like that, then, er, why did you stay in the job?

My husband and I have been looking at condos in the city. Some have 24-hour concierge and valet parking. What are the rules here for tipping? As residents, would we tip each time or just at holidays? What about our guests who use the valet?
M.G. in Cambridge

Oh, how adorable. You and your husband remind me of all those movies of wide-eyed young honeymooners moving to the big city and uncovering its mysteries, just like in Barefoot in the Park. Or Rosemary's Baby. The reason such movies are popular, of course, is because the big city really does conceal mysteries, and proper condo tipping is one of them. Rates and customs vary enormously. In general, people only tip during the holiday season – though some buildings may have a custom of monthly or quarterly tipping. Do tip extra for guests; if they're staying awhile, you might want to give the valet some money in advance to look after them. However, each building is a law unto itself, so ask at the places you're looking into. I've heard that some condo owners won't divulge their own tipping practices, but surely board members can let you know what will be expected. Or you could always find a sweet elderly couple to mentor you and introduce you to the building's culture. Just insist on mixing your own drinks.

My Word
What people who have lost spouses wish everyone knew: People are often extremely supportive when a friend has lost a spouse, but the support needs to keep going for more than the two weeks after the funeral. In the words of reader Kathleen Czerapowicz, "We don't 'get over it'; we adjust to our totally changed lives." (Have you learned something about life you'd like to share? E-mail it to

Miss Conduct is Robin Abrahams, a Cambridge-based writer with a PhD in psychology.

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