Dating has become more sophisticated, if not downright tricky, over the past few decades. It used to be that dinner and a movie or maybe the proverbial long walk on the beach would suffice for a couple just getting to know each other. There are pitfalls, however, as social mores and gender roles have grown more elastic. Here are a few conundra you’ll be hard-pressed to avoid, along with our WhatsYourPrice opinion on the matter.

What we call “chivalry” in the 21st century is a far cry from the “loving but never touching” rules of the Middle Ages, of course. Now there are niceties such as opening doors for one’s date, or pulling out her chair for her in restaurants, or even who pays up when the waiter brings the check.


Still popular, however, is the old “make sure she’s not a witch made of wood” routine.

Opening Doors

This is a classic paradox facing all men and women on dates. On the one hand, opening restaurant or car doors and pulling out chairs shows respect and consideration on the part of the gentleman, and graciously accepting such tokens of chivalry shows class and thoughtfulness on the part of the lady.

On the other hand, however, opening doors and making other moves to show what a chivalrous bit of maleness you are can backfire. Women—and not just those some call “radical feminists”—may feel that they are being treated condescendingly, like they are unable or unwilling to do for themselves. Women may resent the implied quid pro quo this creates: “I’ve done all these nice things for you; how about you doing something nice for me?” It may not even be conscious for either person, but nonetheless it may hang over the date like a pall.


“Wait, I can’t come into the ladies’ room with you? Have you forgotten
how I unlocked your car door?”

So what to do? Act chivalrous (for men) or accept such chivalry (for women), and risk falling into stereotyped gender roles right off the bat? Or acknowledge that women can open doors, go get drinks for themselves, and put their own coats on without manly assistance and risk looking like a thoughtless jerk and adding no value to the date?

Our take: Men lose nothing by starting out a date with opening doors, pulling out chairs, and otherwise acting in a “gentlemanly” manner. If a woman doesn’t care for it, she will let you know.

Paying the Check members pay for the privilege of a first date by making it worth the woman’s while, since new outfits, shoes, makeup, etc. are expenses ladies have for new dates that men just don’t have. So on a date, the playing field is even, with neither party owing anything to the other outside of a pleasant evening.

First dates that happen not to be arranged through WhatsYourPrice are nonetheless in the same situation once they reach the restaurant (for example). Couples on a modern first date have no history yet, no one owing the other.

With this in mind, what happens when the dinner check comes? Serving staff at restaurants used to always give the check to the man, assuming he would be paying for the meal. (In fact, some very high-end restaurants such as Le Cinq in Paris, still give menus with prices on it only to the male, while the woman gets only the description of the food.) These days, the check is usually placed very deliberately in the middle, with the knowledge that either party may foot the bill.

So should a man grab it and insist on paying because he’s the one who asked for the date? That might seem awfully presumptuous. But he can’t really ask the woman if she wants to split it or give it to her to pay without that being agreed upon or at least discussed in some manner. This is thanks to many, many years of tradition: the man is, frankly, expected to pay the check is another arrangement has not been worked out in advance.


“This is her card. I’m very controlling.”

Pay the check or ask for a split or even for the woman to pay? Much like the opening of doors and the pulling out of seats discussed above, what may seem chivalrous to one party may seem rude or unromantic to the other.

Our take: Gents should play it a little ironically. When the check comes, whether it is put directly in front of you or placed in the neutral zone, pick it up and say to your date with a smile, “Okay if I get this one?” It solves both problems, since the man has acted thoughtfully in several ways at once and, since he put it forth as a question, his date can tell him if she’d rather they split the check or even pay the whole bill herself. Win-win.

To Movie or Not to Movie?

As mentioned above, dinner and a movie is a classic and fun date. But paradoxes abound in taking one’s date to the Bijou. First is that while it’s an intimate setting—arms touching, sharing a bag of popcorn, you’re sitting together in the dark, you can sit in the back row, and so on. But you’re supposed to be watching a movie. You could go make out on her couch at home and save $25 if you’re not going to watch the flick!

Of course there is the venerable drive-in movie fooling around, but even then if it’s a first date, do you want to make those car windows steamy on a first date? We advise against it at, since it’s throwing away all that anticipation and replacing it with satisfaction too early, which can make a relationship seem boring just when it could be building.

In any case, some pitfalls with going to a movie on a first date can be:

•  You’re together to get to know each other, yet you can’t talk in a movie

•  The movie could have extreme sex or violence in it or portray controversial political or social viewpoints that would be uncomfortable to watch with a date

•  You might find out your movie tastes are utterly incompatible. This might not matter in an established relationship, but when your time together so far has been half taken up with a movie, if you didn’t both like it or both hate it, that might be seen as a sign to bail before the best part of the date, the walk or drive home where fun stuff—not to mention discussion about a second date—happens.


It’s like you can reach out and touch the awkwardness!

Our take: Unless you both are excited about a particular movie or show (think midnight premieres of hotly anticipated sequels), skip the theater altogether and spend that two hours getting to know one another better.

Competitive anything

You know what sounds like a fun and casual first date? Playing some mini-golf, maybe bowling a couple of games, or even shooting a few hoops. But beware, ye who would enter the world of competitive sports or games on a first date. Here there be tygers.


Also beware, ye who would take a first date to the jungle for some reason.

Why? Any kind of competitive activity which involves two people who should just be having a good time places their date smack into the middle of a paradox: If the man wins, he also loses, because the other party may feel (even if it’s silly) a little sad by losing. A chivalrous man, if he happens to be better at some one-on-one competition, is inclined to “let her win” so the activity stops being about who wins (in his mind, at least) and is more about the fun of the activity itself.

At least, that’s the intention.

Sadly, however, a man who loses at a game or sport loses twice. The gent who lets his date win at, say, air hockey may not seem chivalrous at all, but instead look weak and pitiful. (The woman may not have this perception at all, but the man may think she does, and then it twists off into a tornado of self-doubt and self-recrimination.) If the woman knows she’s lousy at it, she may pick up on him letting her win, and that would be uncomfortable at best and disastrous at worst.

Our take: Don’t do it. Seriously, just don’t.

Chivalry can be fun

Humans are full of paradoxes, believing one thing and doing the opposite, wanting and then not wanting and then wanting again some toy or experience or feeling. In dating, it’s no different. To skirt possible painfully complex issues, treat each opportunity for chivalry as a little bit of fun, and she’ll see that you just want to do what makes her feel good, giving her the occasional opportunity to take her turn opening the door for you. Hang loose and have fun—that always makes for a great, non-paradoxical first date.


Also wine and pizza. Hard to go wrong with that.

What are some of your favorite things to do on a first date?

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