Double-Down On Love: Blackjack Secrets For Better Dating

You know what’s fun? Dating. You know what else is fun? Gambling. Also, dating is kind of a gamble, and Americans have a romance with gambling, so it all fits together like a nickel in a slot machine. Why, then, shouldn’t gambling have something to say about dating? It does, my friends, it does.

My game of choice is Blackjack, and living in Las Vegas I have many opportunities to lose all my money practice my hobby. There are many mathematical subtleties to the game, which I rush to enjoy before my third Mai Tai. After that, it’s all instinct, basic strategy, and a little bit of card counting.


Be aware that this might seem suspicious at the table.

How does Blackjack relate to dating? Other than you’re usually hoping for something under 21 (I kid), there are many lessons that the most popular table game in the world can teach would-be lovers. Place your bets—but follow these gaming tips and you’re likely to end up a winner on your next date.

1. Check Your Bankroll 

In Blackjack, your bankroll for any particular session should be 40 times whatever your base bet is going to be (e.g., a $10 bet would require a $400 bankroll, $15 would require $600, and so on). It’s not required by any means, but it should allow you to play a good long time, and you’re more likely to hit your “stop-win” (see below) than lose all your dough.

It’s the same thing with dating. Whoever is paying for the date—let’s just say the man, since most relationships on dating sites like are rich Sugar Daddies with comely Sugar Babies)—should have a big enough bankroll to weather any ups and downs the evening might throw at him and his partner. Need a table now to impress her? Take a $100 bill and say, “Mr. Bouncer, please meet my friend, Mr. Franklin. We’d like a table near the scenic window.”


Alternately, your friend Mr. Washington can get you a table near the PlayPlace.

Did the Jag get stolen by miscreants? No problem, take a cab—or maybe a limo—while you alert OnStar. You don’t need to liquidate your stocks into cash and carry all of that on you. It’s just best to have enough money in your wallet or on your plastic to keep your date happy and the martinis flowing like wine.

2. Set A “Stop-Win”

In the Blackjack example above, the 40x bet that you bring to the table should be the only money you bring for that session. This is called a “stop-loss,” and allows you not to end up indigent and wearing barrels with suspenders just because you thought you could track Aces during the shuffle.

But there is also the “stop-win,” which I always set at 20 times the bet I will be making. If you like to play the $5 tables, this is $100. Once you’ve reached $100 over your original stake, stop playing. Or only play with the house money you made over $100; this way, you’re guaranteed not to lose that goal amount of money.

It’s the same thing with dating. What’s your stop-win? How much is enough to “win” during a date? Lots of men—disreputable sorts, not upstanding Sugar Daddy types—are hoping to have sex on the first date, rough sex on the second, and weird sex on the third.

furry-fandom-sex-fetishA fox doing a rooster, okay. But WHO IS LISTENING ON THAT PHONE?

Play it like a smart gambler plays Blackjack: Be open to whatever may come your way, but find a level at which you will be satisfied for any particular date during your relationship. If it’s a goodnight kiss, great. If it’s making out, wonderful. Even if it’s full-on donkey-aberrant sex, it’s important to know going in what you’ll stop at and not push things any further.

By the way, “nice conversation and flirting” is a stop-win that’s easy to reach and can make for happy dating in the future. It’s fun to return to the tables when you’ve reached your stop-win and then see if you can hit a new one in your next session.

3. Be Bold … But Not Stupid Bold

Okay, you’re sitting at the felt and the dealer zips you a 10 and a 6. (That’s 16, in case you haven’t had your coffee yet.) Then he shows an Ace. This is the worst situation you can be in as a player against the house. All the books say that you are very probably going to lose on this hand, but there’s a slightly lower chance you’ll lose if you “hit” and risk “busting” (going over 21) rather than just “standing” on your 16.

It’s really hard for many players to hit, even though they know that technically it’s a better move than standing. They hope for the dealer to bust, even though with an Ace showing, this will be only about 12% of the time. (I like the math of gambling. So sue me.)


Mathematics show that this is a great hand in poker, but a less great 41 or 51 in Blackjack.

This timidity will kill players at the Blackjack table and it can also ruin what could have been a lovely date, not to mention nipping any chance of a beautiful relationship in the bud. The waiter very condescendingly sneers at you when you ask for a wine recommendation—what do you do?

Do you meekly say, “I guess that was a dumb question, huh?” Or do you say, “Pardon me, garçon, but take that attitude back to your day job at Burger King. Get me the sommelier.” This second choice is harsh (and witty, but that’s because I had 10 minutes sitting here thinking of a good insult; your improvised results may vary) but it is bold, and you’ve shown your date that you know what to do to get the best. Hitting on 16 gets you the best chance against a dealer Ace; standing up to rudeness gets you the best chance not only of sampling better wine but also of showing your date you are bold.

What you don’t do is punch the waiter in the face or try to get him fired. Bold is good—unbridled rage is less so. You don’t hit on 20 because it’s a bold way to try to get 21, and you don’t ruin the waiter’s life just to boldly punish a snooty jerk.


“HA! How you gonna get to work NOW, Fancy Waiter Man?”

Blackjack: The Second-Greatest Game Ever Invented

The first being dating, of course. So many variables! So many chances to lose or to win! The prize can be life-changing, and the loss can sink players into a deep blue funk. However, taking some lessons from the 21 casino table may be your best hedge against the house when it comes to making your date a success.


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