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Paying on the First Date


It's your first date with a lady. Should you pay for everything? Should she pitch in for part - maybe her food, or drinks? Should she pay if she invited you out? What if you don't like her, or she doesn't like you, and it's obvious you two are never going to see one another again? What other factors should be taken into consideration? I recently queried the readers of The Don Juan Newsletter for their opinions on Paying on the First Date. This is what they had to say.


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Although I've had just about everything else go wrong at one time or another on first dates, one thing I've never had an issue with is determining who pays. To me, it's pretty simple. With a few exceptions, you (the guy) should always assume you're paying for everything. Here are some common exceptions:

1) She blatantly insists on paying for something. (Too bitchy and controlling, drop her like a hot rock. Most likely a closet Melissa Etheridge fan).

2) She had offered to take you out as a basis for the date. (score! :)

3) She makes a concession during the date: "Since you paid the cover, let me buy you a drink." (She's fair and reasonable. Introduce this one to your mom ASAP.)

4) During the date, she mentions that she just got a bonus/lotto winning/raise/etc, and wants to take YOU out. (Tell her that your love just cannot be bought.....yeah right.)

5) Is suggesting or ordering very expensive things, and constantly talking about extravagant gifts she's received in the past. (Obvious golddigger alert. Take her home to the condo that some other schmuck is probably paying for.)

6) You find out your date is actually a guy. (I hope this never happens.)

7) Your date reveals to you that she's actually a nymphomaniac. (Not only do you pay for the date, but the motel room, whipped cream, and live chickens as well.)

Okay, so the last two probably aren't so common..... Keep in mind, that if a woman merely offers to pay for something, she's most likely just being courteous. Politely refuse her offer, and only if she insists on paying should you concede. Besides, it gives you a perfect opportunity to say something cheesy like "Paying for dinner is the least I can do for such a wonderful evening with a beautiful woman like yourself." ;)


If you were the one who invited the lady out, then you should expect and plan on paying the bill. If she would offer to either help pay or take care of the entire bill, then mention that you would like the pleasure of picking up the tab since you did the inviting. Also suggest that her paying for a future date would be fine if she would ask you to dinner, lunch, movie or whatever, and ask whether that type of arrangement wouldn't be fine with her. Then by all means do let her invite you out and pay for the date. If she would then continue to insist then let her do what she would like and look for someone else to date. Hoop


If it's the first date, the guy pays. Bottom line.

The only possible exception is if you're working as a pizza delivery guy or something, and one of your particularly well-to-do customers asks you to spend a weekend with her flying in her private jet to Paris. Other than that, the guy pays.

Even if you two aren't compatible, or will never see each other again, that the guy will pay is all part of the bargain when he agrees for the first time to go out with a lady.

If the date craters, get through it the best you can and behave as you normally would: with civility, dignity, and picking up the check.


I believe that we, as men, should always pay on the first date. It is expected from the woman's point of view and even society. Even if she invites, we should always pay in the first date. I think that by paying we already won a point with the date. Later it all depends on how well we can manage to keep things going without intimidating the woman.


Quite a difficult situation, but as the perfect gentleman, you'd always offer to pay for the meal (and depending on the woman, even be expected to pay!). But in today's society, with women's independence being as high as it is, women are more inclined to say that if they didn't contribute, it would reflect badly on them. It would almost seem as though by just offering to pay for the meal, you were in fact taking away the very essence of their womanhood (sounds a bit over the top, but it can happen).

As a gentleman, I'm the kind of person who would always end up paying for the meal. If you agreed to go out with her, and it didn't work out, wasn't it worth paying for the meal just in case this was the special one?

A chance lost is a chance wasted.


I was always of the mind that men paid no matter what. I'm 41 (a young 41 mind you), and that might color it some, but I always want to pay. It's just the right thing to do. I think deep down, most women want it that way too.


Men should always pay for the first date. Even if the woman offers. If she insists then compromise by offering her the chance to pay on the next date. If you are on a first date with a women that means there is an initial positive impression by both parties. There is always a possibility that you may not like you date or she may not like you. That's a gamble we as men should be willing to take.

Rule of thumb is not to go overboard on the first date just in case things don't work out. Keep it sweet and simple.


Here's the thing with me. While at university I used to pay for everything the first time I'd go out with a girl. I think it is something that should happen in all situations, unless you and she are very cool about being treated as equal. I've only met that in very trendy chicks (DJ's chicks, club bouncers' girls, etc.).

Now my problem is that after I pay for the first time, I'll also pay for the second, because I don't want the girl to think that I like her less. And then the third and the fourth and fifth and so on.

After a few times of doing that and losing my money and the girl's respect at the same time, I decided to only pay for the first time, or at special events where I may want to take her and she wouldn't pay to go there.