Ask the Dating Queen: Dealing with Deal-Breakers and Getting Him to Ask You Out

Today marks the beginning of an ongoing series in which the illustrious Dating Queen (that being me) draws on her vast dating experience to answer the questions of readers in the most queenly of fashions.

In other words, I'll blather on about what I think, and you're free to take it or leave it.

No, I'm not a therapist, but I've done a lot of dating (seriously, 57 men in 2 1/2 years, which by default makes me something of an expert), and I've got me some opinions, which I'm oh, so happy to share.

Wanna play? Just click here and send me your question. I can't promise an answer to every question I receive, but I'll respond to your email regardless.

Now, onto today's question!

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Dear Dating Guru,

I am taking a writing class — there are 8 of us: 2 men and 6 women. One of the guys I find intriguing, not to mention he is a really amazing writer. However, there are a couple of quirks:

• He is (I think) in his 50's — I never saw myself with someone that old.

• He is a teacher — I always thought I would be with someone white collar.

• He is Jewish — I am never attracted to Jewish guys - YELP!

So what should I do? How should I approach him? There are still 2 classes left...

What are your thoughts, oh grand guru gal?

Sincerely,
Perplexed and Pondering

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Dear Perplexed,

Well, gosh, nobody's called me a "guru" before! Now I'm wondering if I should have called this site The Dating Guru...

Nah, being a Queen is way better.

But still, maybe I'll add Dating Guru to my business cards, under Renaissance Woman.

Anyway, the way I see it, you've got a couple of questions here:

1) How do you deal with qualities that have historically been deal-breakers for you?

and

2) How can you get the dang fool to ask you out?

Regarding #1, I say don't let the "quirks" stop you! Your past requirements/deal breakers haven't landed you the partner you want, right?  So maybe it's time to try a different approach, and open yourself up to dating "against type." One of the principles of The Four Man Plan (one of my favorite dating books ever) is to say yes to every invitation, and although it sometimes feels excruciating, it's actually pretty fucking brilliant.

4MP author, Cindy Lu, calls this the "Yes Factor," and until you get really clear about what kind of man is good for you (as opposed to the jerkwads you've probably ended up with to date), it's a solid idea to sample from a larger pool of specimens than you've fished from in the past.

You write, "I never saw myself with someone that old." Okay, I respect that. But maybe it's time to be a little open-minded. Just because you never saw it, doesn't mean it couldn't be okay, right? You're clearly intrigued by him, so maybe his age isn't as much of an issue as you thought. You may decide down the road that no, this guy is too much of a geezer for you, but you don't have to make that decision right now! In fact, it's better not to limit your pool (see above).

And in any case, none of this is really about him anyway. The goal right now is to just get a damn date (and hopefully a few more with other guys, too, so you won't get all obsessive about the first guy before you can tell whether he's even worth obsessing over [scratch that — nobody's worth obsessing over]). THEN you can do more assessing about whether this guy is someone you want to spend more time with or not.

In The 4MP, you keep track of the men on your radar with a 4-square graph; a man you've exchanged contact info with is worth 1/4 of a space on your graph, so collecting guys to potentially go out with is referred to as collecting Quarters. Thinking of it that way takes a helluva lot of pressure off. It's a lot like finding spare change on the ground; a quarter may not be worth much, but you never know when it might save your freakin' butt, by helping you get your laundry done, or filling up your parking meter.

When you go on a date with a Quarter man you're not interviewing a potential life partner; your goal is not to determine whether the dang fool across the table from you is someone you want to spend your life with, but just to see if you could stomach another date with him.* (And of course to have fun!)

Now let's talk about Writing Class Guy's profession. Yeah, you probably fantasize about some Wall Street God who (if he hasn't lost his life savings in the Crash) will come home in a monkey suit before sweeping you off to a fancy dinner at Chez Panisse. But what's really important here? Money? The kind of car he drives?

What if this guy (or some other teacher, or a mechanic, or whatever) turns out to be the love of your life, who will treat you like the amazing goddess you are (not to mention being a superhero in bed), but you pass him over entirely simply because of his job? That would SUCK, no?

So just get down with the fact that the universe has a sense of humor, and is guaranteed to incorporate at least a few of your "deal-breaker" qualities into the guy who's your bashert. It's like Murphy's Law, and the sooner you stop resisting it, the sooner you can welcome Mr. Right into your life.

And though you've never been attracted to Jewish guys in the past, you're clearly attracted to this Jewish guy, so that one's just a non-issue. Seems you're now able to be attracted to Jewish guys. Go you! That widens the pool, doesn't it?

As for question #2, that one's harder. I know it's old-fashioned, but I'm of the "let the guy do the inviting" school of dating. Granted, I only asked one guy out on a first date, so I don't have a scientific view on this, but that one time was a disaster that I never want to repeat, and my goal is to save you similar pain. Besides, I'd personally rather be pursued than do the pursuing; if a guy isn't interested in me enough to pursue me, then fuck him! (Or rather, not.)

However, that doesn't mean you can't make it clear to him that you'd be delighted if he were so inclined as to ask you out!

You don't want to be pushy about it, or make it look like you're all over-eager, because nothing will turn a guy off faster. But you can continue to engage him in easy conversation, and maybe even throw out an "I'm headed to So-and-So Bar/Cafe/etc. after class, anyone want to join me?" Give him opportunities to easily spend more time with you. Or if, say, you and he are talking on your way out, you can address this to him alone.

You can also throw light compliments his way, if it seems appropriate and not like you're going to come off as Obsessive-Stalker-Girl. For example, in direct response to something he's said, you might say "I like the way you think!" or "You're really fun to talk to! I wish this class weren't ending so soon!"

These are just generic suggestions, and obviously you'll have to do some thinking about what might work best, AND you'll have to use your super-intuitive goddess powers to figure out when is the appropriate time to say something. It will, by its nature, be improvisational, so take a tip from the Boy Scouts and be prepared with some possible lines to use, but ready to go with the flow. Watch for an opening where you can smoothly throw in your line.

And if Mr. Writer Man doesn't jump all over the bones you're tossing his way, it's likely he's just not into you. Don't sweat it — you want, and totally deserve, someone who is totally into you, so let him go and set your sights elsewhere.

Whatever happens, think of this as a great stepping stone in your path to finding yourself while looking for love. You'll probably learn a ton from whatever happens, whether the guy reciprocates your interest or not. And then you'll be that much better prepared to bring in the relationship of your dreams.

I hope this helps! Let me know how it goes!

Kisses,

The Dating Queen
now aka The Dating Guru

*Which brings me to another principle in The Four Man Plan that many gals resist, to their detriment: the Two Date Minimum. I know, I know, sometimes you really just can't stomach the idea of a second date with someone. Believe me, I've been there! But you wanna know a secret? Half of the women who are now happily married couldn't stand their husbands when they first met them! Okay, I don't actually have data on this, but Lu polled 20 of her happily married friends, and that was indeed what she found. Plus guys get really nervous when they're attracted to a girl, and tend to act all weird, and do stupid things. So give the poor slob a chance. Unless he's married (or has a girlfriend), an addict, abusive to you in any way, or otherwise seriously icky, let him take you out again. Even if you still can't stand him at the end of the second date, you may learn something about yourself. And isn't that what it's all about?

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