What can I say, I enjoy Woody Allen films. And when I recently watched his latest, "Vicky Cristina Barcelona," it made me think. I'm not going to spoil the plot for you, but there's a key question that runs throughout this film. This is by no means the first movie to explore this question, but somehow Allen captured it on a visceral level in this one. And here it is: When it comes to romance, is it better to go for someone who's safe but a bit dull or is it better to set your expectations high and shoot for a partner who's exciting if unpredictable?

This is one of those questions that you can ponder from different angles, compare the pros and cons, and still not be able to arrive at a perfectly sound answer. Philosophically, it's complicated. But there's a certain catch to the question. If I shift gears and think about it as a therapist, I start seeing it as a trick question. So let's say a client came in and asked me, "OK, there's these two people I'm thinking about dating. One is really nice but can be a little boring sometimes, and the other one is really interesting but is all over the place--which one should I go for?"

In that case the question loses its inherent ambiguity. My instant answer, at least in my own head, is "Neither one sounds good." After all, why would you want to go out with someone who you're already perceiveing as boring? And, as for the other one, if you're picking up signs of unpredictability and being all over the place so early on, what's up? Why not look for someone who's safe, nice, exciting and interesting? In other words--Why settle?

When I share these thoughts with clients, I often get a response of, "Well, I don't want to be too picky."

And I come back with, "But I want you to be picky. I want you to find a good match."

When I prod, I learn that the "Don't be picky" advice is often traced back to an old relative, a nosey roommate, or an antsy friend: "My grandmother told me I should give people a fair chance;" "My roommate says my standards are too high;" "My friend tells me I expect too much of others." And of course the list of sources is not limited to these acquaintances. Even parents have been known to meddle: "My mom's afraid that if I don't find somebody soon, I might end up with no one."

As a therapist, though, I can't imagine encouraging a client to date a compromise. Over the years, I've heard many stories from clients who settled for someone who's "OK, I guess" only to end up regretting their decision: "What was I thinking? I should've known better..." But I've never heard anyone say, "Boy, I should've settled more. I really should've lowered my standards."

So what's going on here? Why does being picky carry such a negative connotation?

I think compromise and settling is a crucial part of being a successful person. Maybe this driver took my parking spot, but I'll swallow my pride and settle for another. Maybe my coworker took on the good project and left me with the so-so one, but next time I'll make sure I get first dibs.

But with finding the right romantic relationship, it's different. When people compromise their standards, they do so because of loneliness (e.g. "I really want to be with someone"), time pressure (e.g. "I'm getting older, and time is not my friend"), and opportunity cost (e.g. "If I say 'No' to this one, I may not be able to find someone better.") It comes down to fear: the fear of being lonely, the fear of running out of time, and the fear of missing out on an opportunity. And then it's no longer about who I'm dating, but it becomes about what I stand to lose. Dating takes on the feeling of a chore.

Instead of a fear-based motivation, I'm always curious to hear my client's description of who they're really interested in. "If you could go out with someone who'd really be a good fit, the ideal person, what would that person be like? Describe them to me."

It can be difficult to pin down because a lot of times we don't even take the time to ask ourselves what we really want. Is it important to me that the person be creative? That they're outgoing? What's my type as far as looks go?

A lot of times people don't like thinking about the physical qualities. "I don't want to be shallow." But physical attractiveness is not just about looks, it's about how the person is coming across. If the person's nice but there's no attraction, well, they might make for a really nice friend, but it wouldn't be fair to you or to them to pretend you're feeling it.

When the right person comes along, there's excitement and it's thrilling and you don't have to convince yourself that you should go out with them. Fear, though, sneaks back in--on a completely different level. And then we wonder, "Well, what if I ask them out and they say, 'No.'?"

The dreaded "No." I think it all comes back to Jr. High and High School. It's the fear we had when we were young that if we asked out the wrong person, then everybody would know and we'd become a running joke. Now, the thing is, that if you're being really picky, chances are you're going to get many more "No's" than you will "Yes's." After all, you're taking a chance, and the person might already be in a relationship or they might just not be interested. But that's the whole point: you're not going for the sure bet.

It basically means taking a leap. You're going for your dream partner. It's like what the Danish philosopher Søren Kierkegaard said, you take a leap of faith and you may not make it, but at least you took that leap. And here "not making it" simply means dealing with rejection, which makes us stronger in the long-run anyway.

This reminds me of a group therapy I co-led a long time ago for people who were dealing with shyness and as part of the group we did all these embarrassing activities out in the "real world" of singing songs in public or trying to sell a free daily newspaer for $20 to curious passersby. (No, no one ever took the bait). The whole point was to get rejected and see that the world doesn't end when that happens. All of us, including the therapists, took part in these activities, and I remind myself of it whenever I find myself in a situation where I might come across as being ridiculous. Hey, it builds character. People don't care as much as you think they do.

But being picky instead of operating out of fear becomes a completely different way of thinking about relationships. Instead of trying to find someone who's going to "work," you're searching for someone who's going to mesmerize you. And if you can get into that spirit, the process itself of finding that person becomes exciting in its own way.

Of course, sometimes you think you found the right match, but when you get to know them better you figure out they're not everything you thought they'd be. Well, that's when you have to stay picky and re-evaluate what's going on. It's not easy, but if you see it's not working, it's time to walk away. Being picky is not just about the initial asking out part, it's about the entire process of getting to know someone. And that's why being aware of former patterns in relationships comes in. If in the past I used to date people who had a quick temper, then let me make sure this time that this person doesn't show signs of being curt or easily angered. Or if I was attracted to people who were distant, and this person shows signs of being cold, let me re-consider what's going on.

Here's the thing about being picky: it forces you to have high self-esteem and you build a great connection with your own self: you build your own voice of what you want and what works for you. Yeah, it does take patience and some time to find the ideal person, but it's one of those instances when it's totally worth it.

About the Authors

Ori Brafman

Ori Brafman is the co-author of two books, The Starfish and The Spider and Sway: The Irresistible Pull of Irrational Behavior.

Rom Brafman

Psychologist Rom Brafman has a private practice in Palo Alto, California; he's the co-author of Sway: The Irresistible Pull of Irrational Behavior.

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