In my recent interview at HuffPost Live, I described the One-Night Stand as a “high risk maneuver” when used in hopes of procuring a relationship. That got me thinking – we generally expect greater risks to yield greater rewards, but we forget that few risky strategies ever pay off at all. For every Olympian who embraced enormous risk and was rewarded with victory and fame, there are thousands who took the same risks and failed. As David Epstein writes in The Sports Gene: Inside the Science of Extraordinary Athletic Performance, 10,000 hours of practice helps, but our individual genes define the ultimate limits of our achievement.

Similarly, our wiring, including our comfort with risk, defines our mating strategies in large part. A recent study found that 19% of women (of all ages) have had first-date sex lead to a relationship at least once. We don’t know what percentage of women wanted that sex to lead to a relationship, but based on other research we can safely estimate that many women were disappointed by the outcome when ONSs fizzled.

On the flip side, one can also play it too safe by adopting risk-averse strategies. In my view, the best example of this is the woman who enjoys the benefits the Women’s Movement has delivered, but still believes that men should do all the asking and paying when it comes to dating.

Each one of us must find the approach that works best for us, given our tolerance for risk. We’re likely to benefit from a diverse portfolio of strategies and tactics, with some play-it-safe approaches, some willingness to put ourselves out there, and the occasional high-wire act. Just for the sake of illustration, let’s say you have 100 points to “spend” on your portfolio, and each level of risk has a different price.

Easiest_Ski_WJ89 begin skier

COST: 5 POINTS EACH
Secretly crush on a cute guy.
Act friendly and smile with someone you like.
Meet guys via a shared interest or activity.
Always wait for the guy to make the first move.
Date within your close social circle.
Date guys whose families or reputations you know well.
Date guys with a demonstrated preference for relationships over casual sex.
No sexual activity until relationship is official.

More_Difficult_Ski_WJ74Intermed skier
COST: 10 POINTS EACH
Initiate flirty banter.
Tease him playfully.
Date guys from work.
Give your number to cute guys you meet out.
Try online dating.
Meet guys via your extended social circle, e.g. house parties.
Escalate emotionally when you like someone.
Directly express interest in non-casual relationship.
Engage in some sexual activity prior to DTR talk.


Most_Difficult_Ski_WJ75Dangerous-Ski-Slope
COST: 25 POINTS EACH
Aggressively and sexually pursue the guy you want.
Hook up with guys who have girlfriends.
Hook up with random guys you meet out.
Date a friend’s ex.
Date an ex’s friend.
Have a ONS.
Hook up drunk.
Get with a player.

Now let’s consider the strategy portfolios of three different hypothetical women:

Big Air Blair Blair hooks up with player types almost every weekend, usually after getting wasted. Leaving nothing to chance, she makes a beeline for the hottest guy in the bar and flirts intensely. Her go-to move is to run her hand lightly over the guy’s genitals while tilting her head to one side and grinning.

Aggressively and sexually pursue the guy you want: 25 points
Hook up with random guys you meet out: 25 points
Have a ONS: 25 points
Hook up drunk: 25 points
Blair’s Total Cost: 100 points

Chance of emotional involvement leading to relationship: Extremely Low

Note: It’s entirely possible that Blair has no interest in a relationship, but prefers one-off sex with men she finds attractive. If this is the case, her strategy is likely to succeed.

Mogul Maddie
Maddie is well-liked and gregarious. She enjoys receiving attention from guys, and loves to socialize. She’s had a fling or two, but she’s not really the promiscuous type. She would like to have a serious relationship.

Act friendly and smile with someone you like: 5 points
Meet guys via a shared interest or activity: 5 points
Date guys with a demonstrated preference for relationships over casual sex: 5 points
Initiate flirty banter: 10 points
Tease him playfully: 10 points
Give your number to cute guys you meet out: 10 points
Try online dating: 10 points
Escalate emotionally when you like someone: 10 points
Engage in some sexual activity prior to DTR talk: 10 points
Have a ONS: 25 points
Maddie’s Total Cost: 100 points

Chance of emotional involvement leading to relationship: Moderately High to High
Snowplow Sofie
Sofie is fairly reserved and quite pretty. She’s not very comfortable taking risks in social situations – she prefers that confident guys make their way to her and express their interest. This works well in that she often has guys flitting around her, but nothing seems to stick. She has a lot of first and second dates – the guys always pay – and then they tend to disappear.

Meet guys via a shared interest or activity: 5 points
Always wait for the guy to make the first move: 5 points
Date within your close social circle: 5 points
Date guys whose families or reputations you know well: 5 points
Date guys with a demonstrated preference for relationships over casual sex: 5 points
No sex until relationship is official: 5 points
Date guys from work: 10 points
Give your number to cute guys you meet out: 10 points
Try online dating: 10 points
Sofie’s Total Cost: 60 points

Chance of emotional involvement leading to relationship: Moderate

Note: Sofie has 40 unspent points. She would never feel comfortable having casual sex, but she might broaden her horizons a bit by taking on more risk. For example, she could add:

Tease him playfully.
Escalate emotionally when you like someone.
Directly express interest in non-casual relationship.
Engage in some sexual activity prior to DTR talk.

Adding in these behaviors might significantly increase Sofie’s chances of getting a quality relationship.

If you want a meaningful relationship with an attractive man of good character, you’re most likely going to need to take some risks. Take the bulk of your tactics from the middle group, sprinkling in safe bets as appropriate, and indulging in the riskiest strategies sparingly, if at all.