A Numbers Approach to Finding True Love

We’re coming up on Valentine’s Day, when the young (and old) hearts and thoughts take a romantic turn. In this spirit, my posts for this week and next will all involve love and personal finance. If any other bloggers want to join in on the fun, please send me a link to your post at and I’d be happy to profile what you’ve written.

As I alluded to in my economics of dating post, I have an approach to dating that I’ve used and have recommended to friends which I think would be useful to many people who are unhappily single.  To be completely upfront, I’ve never been married (and have only lived with one woman for a brief period of time).  However, I’ve dated a reasonably large number of woman (enough that I’m not sure the exact count at this point) and have had a few women who would have been willing to marry me, so I stand behind this.

For anyone who questions if dating advice belongs on a personal finance blog, who we marry (and whether we stay married to them or not) MASSIVELY affects our financial situation.  Along with career choice and spending habits, our partner is probably one of the biggest determining factors in personal finance.

The first element of this is that the date-seeker needs to get rid of any idea of “soul mates” or “their type”.  I suspect that over the course of a lifetime we all meet 100-200 people we could probably have a reasonably happy life with.  It’s ok to find some characteristics attractive (personally I really like redheads – yum!), but if you become fixated on something as an absolute requirement, and there aren’t many people who fulfill your requirement, you’re setting yourself up to be alone.

As an example, many woman want a guy who is taller than them, earns more money than them and has nice hair).  That’s great unless you’re a tall, successful woman and you’re competing with similar women for the same small pool of guys.  If a guy’s only demand is that the women he dates be swimsuit models, he’s got some long, lonely nights ahead of him.

Some people say “be picky, you’re worth it!”  If someone wants to be dating and they aren’t, then they’re being too picky.  Of course, if someone would rather be alone than compromise, that’s totally cool but they need to own that decision (they’ve chosen to be alone:  no complaining 🙂 ).

The second element that needs to be jettisoned is the idea that singles can sit back and wait to run into Mr. or Mrs. Right.  They can’t.  All sorts of people never get married and they cop out later in life with the lame excuse “I just never met the right person”.  Bullshit.  They needed to go out and find the right person (and instead, unwisely, chose not to).

Once these two ideas have been abandoned, the date seeker just needs to find enough prospects to ask out in order to find enough people to date seriously in order to find someone to propose to who’ll say yes and get married to them (it’s as easy as that!).  Think of it as a pyramid or a weeding out process where the most important part is the number of prospects (there needs to be enough of them to find that special someone).

I once read about a psychologist who got tired of his clients saying “no one will date me” and he ran an “experiment” where he would walk up to women and ask them if they’d go out on a date with him (no cheesy lines or anything, just walk up and ask).  It took him 50 tries, but eventually someone said yes.  I don’t know how good (or bad) looking he was, but I think this would probably be true for anyone (eventually someone will say yes).

Fortunately, technology makes things even easier.  Sign up for, eHarmony, OkCupid and Plenty Of Fish and send messages to 3 people a day.  That’s 21 people a week or about 90 a month.  Push through the pain of rejection or fear and eventually there will be dating.  Say 1 in 10 people messaged on OkCupid will respond and meet for coffee, 1 in 10 people met for coffee will go on a second date, and 1 in 5 of these people dated a second time becomes a serious relationship leading to marriage.  This implies 500 people need to be messaged to find true love.

I’m somewhat (not completely) sympathetic to women who aren’t willing to ask men out or initiate contact on dating sites (so women can lead G8 countries, but can’t ask a man out on a coffee date?  RIIIGGGHHHTTT).  If someone decides they aren’t going to do the asking out, they have an obligation to make it very clear that they’re available, single, and likely to say yes.  I’m not sure the exact mechanics of this (I’d appreciate any women who can make suggestions in the comments), but the nearest I’ve figured it out is that it involves smiling a lot and working into the conversation that she’s single (“well, as a single woman who isn’t seeing anyone right now, I have a particular interest in whether or not Greece is on the verge of bankruptcy…”).

For guys who think they’ll be destroyed (DESTROYED!) by a woman saying no to them:  you won’t be.  Man up!

If you’re married or in a relationship, what’s your favourite piece of dating advice?  If you’re (unhappily) single what’s been preventing you from finding someone?

14 replies on “A Numbers Approach to Finding True Love”

Fantastic! I agree that you have to aggressive and just ask, hard as it may be.

I know a guy who will only date Asian women. He was married once (mail order) and oddly enuf things fell apart once she got to Canada and didn’t need him or his $$ anymore.

If you ever watch the movie Up in the Air, there’s a scene where the twenty-something and the thirty-something year old women discuss what they want in a man. It is a brillant construct on the idea of “settling” in life and how perspectives change with life experience.

My only piece of advice as a single guy is make your intentions clear up front (one night, multiple nights or multiple years?). Good luck with the redheads!

Mike: Same thing happened to a friend of my brother.

TMW: “Up in the Air” was fantastic (and you’re right, that was a great scene). Making your intentions clear is good advice…

As a female who found herself among those who didn’t prefer to initiate, I second the advice aimed at males to man up!

Before we were even dating, my now-husband informed me he was going to marry the crap outta me.

He did. 🙂

Hey Mike

So it’s a numbers game – is what you’re saying, yes? The more you put yourself out there, the more likely you are to get a yes amidst the no’s?
Pretty much the same principle salesmen and cold callers base their pitches on – huh? Is being persistent what its about?

Be yourself. And look for someone who’s comfortable enough in their own skin to do the same. I was 19 when I met my husband, and I had just broken up with someone else. The last thing I wanted was to start another relationship.

I agreed to dinner with him because he seemed like a decent guy and I needed a distraction. My guard was down and I made no effort to impress him whatsoever. It turns out he liked me for who I really was. The feeling shortly became mutual, and 3 kids and a total of 20 years or so later, we’re still here.

The moral is, if you are true to yourself and find someone else who is the same way, there will be no nasty surprises years down the road. To this day, I cannot understand why my husband finds some of my more annoying qualities so amusing, but he does, and I’m really grateful for that.

I agree that it’s a numbers game. The more people you meet, the more likely you’ll find one that’s a great match. (also, you will quickly find out what you must have and/or can’t stand in a member of the opposite sex). I also agree that there is no one soulmate for you. There’s dozens of people you’ll meet throughout your life with whom you could have a long and fruitful life together. Its just a timing thing.

I didn’t do any real dating until after university, and then I signed up for lavalife. I probably went on dates with close to 100 people (all through lavalife). The majority, it was just a first date and thanks see you later, others it was a few dates, and a handful it turned it to months or year long relationships. And the last one is the one I ended up marrying (I was the first person she met online, so her standards must’ve been pretty low).
I don’t regret it for a second. Sure, I spent a lot of time in coffeeshops. But I met a lot of great people, some I am still friends with. And if you go through enough dates, you actually get pretty good at the whole interview process and interacting with strangers. That was something I wasn’t good at before, so if I got nothing out of it, at least my soft skills improved.

Definitely, what you are looking for changes over time. It used to be a slim, classy, intelligent girl. Now it’s someone who can make me laugh and has great relationships with her friends and parents. It changes as you meet people who you thought were perfect for you end up feeling hollow. Or when you meet someone you weren’t expecting to hit it off with, but you discovered what you were really looking for in a mate, but didn’t know it.

I read “He’s Just Not That Into You” for a laugh and it enraged me that the author insisted that women not make the first move. The general message in the book is that a woman can sucessfully initiate a relationship, but if the man is truly and deeply interested, he will always find a way to do it. Therefore (according to him) if a woman is looking for a serious relationship, she should hold out for a man who is willing to make a move himself because she would be wasting her time if she pursues a relationship with someone who wasn’t “into her” enough to do it himself.

The “take no crap” approach was refreshing, but I just couldn’t agree with the advice to always let the man do the work. Unfortunately, I can’t produce any personal experience to refute this idea. It so happens that my husband pursued me and that past relashionships where I aggressively pursued someone crashed and burned terribly.

My general advice would be to make eye contact (without staring!), smile a lot and be yourself.

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