Monday, September 14, 2009

That Dreaded Question …

You’re on a wonderful date (finally!). You’re laughing and having fun. You are super attracted to your date and there’s no question that there’s chemistry. You’re even reaching over to try each other’s entrees with the familiarity of at least date 2 or 3. There’s no lull in the conversation. And then he/she asks:

“You seem so amazing, you are so much fun and, you know, of course, you’re very cute … HOW are you still single?


If you’re under 30, chances are the question rolls off your shoulder with a knowing smile, a thank you and a cheeky shrug. If you’re over 30, the arms cross and the eyes narrow a bit. You know that the question is “supposed” to be flattering but it has the inherent effect of making you feel instantly defensive. This question is supposed to be a compliment?! Rather, reading between the lines,* the question could be heard like this:

“You seem so amazing, you are so much fun and, you know, of course, you’re very cute … There must be something wrong with you if you’re seemingly so amazing and STILL single at [insert age]. What am I missing? Come on, tell me what it is so I don’t have to waste weeks trying to figure it out.”

Possible responses swirl in your head.

You could answer with the generic interview-style response: “I’m just very picky.” Aren’t we all … and I’m too detailed oriented.

Or you could offer the comical “deflect the answer” type response such as: “I’m really an ax-murder so none of my relationships have ever gotten very far.” Or “I’m just too good for you girls/guys.” ** Perhaps it will get a laugh.

Or maybe you try the “turn the tables” approach: “Well, you’re single too, so what’s wrong with YOU?!” I don’t recommend this one for obvious reasons.

Most of the time the person asking the dreaded question is in fact trying to compliment you (and figure out what could be wrong with you) but doesn’t realize that the question can make dates feel like they have to justify their single 35/40/45/etc. year old existence. When I told one of my girlfriends the topic of this week’s blog, she remarked “that question is downright rude.”

Yes, perhaps it is rude – even if it’s not intended to be. Regardless, it’s certainly not a smart question for a first date. Does anyone think they are going to get an honest answer? There are many reasons why someone as wonderful as yourself could be single at 30+, 40+. Are you going to get into the details behind such a personal issue with someone you barely know? A good response to this typically well-intentioned inquiry can be simple and straightforward: “I’ve had some wonderful relationships but none of them were right for the long run. In my opinion, marriage isn’t something to be taken lightly. I want to make sure it’s right.” A fine answer and, hopefully, this is true. Anyone who has ideas for a good response, please post them – at a minimum, we’ll all get a good laugh.

But while my dear readers (and I know you’re out there and growing - thank you!) are stopping to think of what witty answers they might offer should this question rear its ugly head on their next romantic encounter, it also does calls for a moment of true reflection.***

If you’re single and don’t want to be, why not take a few moments and really ask yourself the dreaded question: Why am I still single? (if you’re single and happy about it, feel free to clap your hands and stop reading now).

Maybe you are too picky … but maybe picky is a nice way of saying unrealistic. Maybe you’re not “getting” the same guy or girl you were “getting” five, or even two, years ago – at least not for the long run. There could be a variety of reasons for this. Maybe it’s time to face reality. If you’re a woman in your late 30s perhaps it’s time to expand the age of the guys you’ll consider dating – there are a whole lot of good guys out there who may surpass the 4 to 5 year cap you’ve arbitrarily placed. It may also be time to really ask yourself why it’s so important that the guy towers over you? Yes, tall is preferred (sorry short guys, it’s true). But there are a lot of women married to tall men who would give anything to be with their friend’s short, but caring, kind and considerate husband. And if you’re a guy who has “dated” “hot chicks” but has actually never had more than a one night stand with one, maybe it’s time to ask why you keep going for the model types? Are you really looking for a partner or for validation?

Maybe it’s time to take stock of your dating life. Is it possible you’re doing something wrong or something that is sabotaging your chances of meeting the person who is right for you? Yes, time for a small plug for my business. I give my clients feedback (often straight from the person that they have been introduced to) that friends and family are simply not going to tell them. Tough love with a gentle hand. Recently, I spoke with a guy who had expressed an interest in becoming a client. He explained to me that he wanted to hold off on joining as he had recently been on “a million dates” and that he had a "million more" in the pipeline. I thought, if I were going on dozens and dozens of dates and none of them yielded a match I would consider that a bad thing – clearly something is not working, shouldn’t it be time to find out? Unless you’re dating for the hell of it, which I know this particular guy is not.

For all the people reading this thinking, “well, my answer is simple – I just don’t want to settle” - try a little exercise. Think of your best single girl or guy friend. If someone were to ask you why “Jane” or “Joe” is still single, I imagine you probably could offer a very informed opinion. And something tells me it wouldn’t be simply that Jane and Joe just don’t want to settle (though, most likely that would be their answer). Now what if someone asked Jane or Joe about you …

*Yes, it’s been a while since we had fun researching expressions just for the heck of it. This particular phrase comes from the days of military letters and writing, which were often written in a coded form. According to The Phrase Finder, this phrase “derives from a simple form of cryptography, in which a hidden meaning was conveyed by secreting it between lines of text. It originated in the mid 19th century and soon became used to refer to the deciphering of any coded or unclear form of communication, whether written or not.” Ok, this one’s not that surprising …

**Both of these are used by male friends of mine. I add this to ensure my female readers that men get asked this question just like the women do.

***This weekend starts the Jewish high holidays. I love this time of year because it ushers in a week of reflection. Even if you don't observe these holidays, there’s nothing stopping you from asking yourself some soul searching questions. Summer’s over and it is a new season, after all.


  1. there's something arrogant about this article... too confident about tall guys preferred (not short here)... and the whole issue is really trivial.

  2. there's something arrogant about this article... too confident about tall guys preferred (not short here)... and the whole issue is really trivial.

  3. Thanks for your comment, Jack - all comments are appreciated. What you consider arrogance is not coming from me per se but from the countless women I speak to - perhaps as a tall guy you don't have as much exposure to this issue as others. Regarding your feeling on the trivial nature of the question, it is a question that taps into many profound (and anything but trivial) feelings that single people feel out there when asked that question. My goal is to keep things light- hearted while addressing serious dating issues. Hope you keep staying tuned and adding to the discussion!

  4. It's interesting but even if we don't say it aloud I think we've all thought that about someone we're out with for the 1st/2nd time. It might be a bit cynical but heck, this is NY. Much like in Seinfeld when Jerry's Uncle says to Jerry that he "Found the perfect woman" and "doesn't see a flaw" in her - to which Jerry replies "Well, keep looking." And this really drives your point home - if we set our standards so ridiculously high we'll give-up the chance of finding someone very special...which is no trivial matter ;)

  5. “You seem so amazing, you are so much fun and, you know, of course, you’re very cute … HOW are you still single?”

    I'm still single because I've been waiting to meet someone like you.

  6. That's a very good one - should definitely bring about a smile!

  7. Also, I wanted to thank Anonymous who posted the very appropriate Seinfeld reference! Yes, I think as New Yorkers we are inclined to seek perfection and have very high standards - but, yes, at some point it becomes almost absurd. Recognizing the overall good in people and being able to accept others' faults (as we all have our own), is what increases one's chances of finding someone who can truly be a partner. And thanks for the trivial reference - it was not lost on me and was much appreciated! I agree entirely - what's at the heart of "the dreaded question" is no trivial matter.