Category: date etiquette

  • Nine ways smart women sabotage their own love lives

    Since I moved to San Francisco, I’ve noticed that there are a lot of great women who are still single. On the one hand, it’s good for business, so I can’t complain too much. On the other hand, it saddens me because many of these women are so fantastic – smart, funny, beautiful – and really don’t want to be single. Not forever, at least.

    It’s probably true the guys you date are partly to blame here. However, every relationship you’ve been in has one thing in common: YOU. So maybe it’s time to take an honest inventory and see if you’ve been engaging in any of the following self-sabotaging behaviors I’ve observed that inadvertently drive off the good guys who already like you (NB: most of these are applicable to men, too, so listen up, gentlemen):

    1. You don’t show up.

    Let’s face it: dates are weird. And it’s perfectly normal to feel some trepidation at the prospect of spending time with a stranger. Especially if that stranger is (more…)

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  • Mailbag: On handling players, touchy questions & how to ask a guy out

    Well well well. After that last ‘Mailbag, Uncensored’ piece that I sent out, I found myself inundated by your letters. Deluged. Flooded. Well, to the extent that bits and bytes can flood an office, that is. Still relatively dry around here.

    Now, of the dozens of letters I got, not one of them adhered to the length guidelines of 5-10 lines. Novellas and full-length sagas all around.

    People! The story doesn’t have to begin in the 5th grade, when little Johnny teased you about your frilly pink shoes and you’re still not over it. Summarize. When you put in the effort to summarize the situation, you actually figure out a lot about what’s going on, what matters and what doesn’t. Otherwise you’re just putting all the onus of figuring out the situation on me, which is not helpful. Same with the perennial “What should I do?” non-question.

    So the new guidelines: explain your situation and formulate your specific question in 250 words or less. Otherwise there’s no human way for me to get to all of them.  Awright, let’s start: (more…)

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  • The Praise Sandwich and how to deal with Octopus Man

    Hi Dr. A:

    I had a second date with a guy on Sunday that I think I could possibly like–I certainly admire his work and his work ethic. BUT on our second date, we had a make out session but then suddenly he turned into octopus man and actually found out what color bra I was wearing!  I wasn’t prepared for that and now am feeling slightly resentful and guilty and angry and wondering what I did. Yes, I kissed him passionately for minutes at a time. Was that it? Now that it’s done–I won’t see him for a couple of weeks (he’s away working.) That doesn’t bother me (yet.) My question is: How can I tell him I’d like to take things more slowly. I don’t want to cut him lose but he’s moving a little fast.

    What’s the nicest, most encouraging thing I can say to him to get my message across without hurting his feelings or chasing him away–which I don’t want to do. I suppose just being honest about my feelings (in a nice way at the right time) would probably be the way to handle this. Just wondering what you think?

    Thanks from a big fan, Jessica

    Good question, Jess!  Your inuition is correct: tell him that you’d like to take things more slowly — y’know, as opposed to just thinking about telling him.  Communicate!

    For difficult conversations, I like to use the Praise Sandwich: start with praise; say what’s on your mind (usually less pleasant than praise); end with praise.  People tend to remember the first and last items in a list best (primacy and recency are the technical terms), so he’ll leave feeling good about the whole thing.  In the meantime, you deliver your message successfully.

    Also, in the letter it sounds like you’re blaming yourself for his ‘octopus’ behavior.  From here, it sounds like he did it, and it’s probably because he thinks you’re hot, which is a good thing.  Some day you’ll be 90yrs old and wrinkly and wish guys would make passes at you.  Resentment, guilt and anger would be (more…)

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  • Seven things smart women should never do on a date

    I believe that smart, fabulous, successful, attractive women deserve fulfilling, deliriously happy love lives.  Sometimes, though, unintentional behaviors ruin our chances in courtship.

    In compiling this list, I’m speaking as an author who’s been on the receiving end of hundreds of guys’ letters on their dating woes — and a single guy who’s been on a bad date or two. So what I’m telling you here is straight from the horse’s mouth — if horses had graduate degrees and spoke in complete, remarkably coherent English sentences.

    Also note that the subject of this article was framed negatively to get your attention. Now that I have said attention, I will frame the items positively — things you should do. Tends to be even more useful.

    So, you’re ready? Here they come:

    1. Do everything in your power to keep the first date.

    So your guy met you at a party somewhere. He stuck his neck out and wrote the first email, made the first call, and set up the first date.

    Sure, you hit it off when you first met, and it was fun talking to him on the phone.  But right now, as the moment of truth draws near, you just feel like you need to cancel or postpone. Excuses to cancel seem to be cropping up by the minute.

    And you know what?  That’s normal.  The temptation to cancel the first date at the last minute is (more…)

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