ArticleDating Advice

Who Should Pay on a Date?

I can usually weed out people on Tinder within the first five to ten chat messages. And that’s what happened a few months ago with Jeff. I quickly decided I never wanted to meet this guy, but as it turns out, Jeff and I chatted nearly every day for a week. Why? We were debating as to whether a guy should pay for a girl on a date. Needless to say, I have something to say on the topic.

The truth is, deciding where to go and who’s paying for what can lead to awkward or uncomfortable situations, so here are some tips:

Take Control

This may not be the answer you want to hear (or read), but as a general rule, just pay for the first date. Do not, however, spend outside your budget.

If you’re an online dater and it will be the first time you are meeting a girl, this is not a time to wine and dine. This is a time to get to know each other, so treat it like that. Meet at a cafe or a park and buy her a drink. Then decide if you want to take things further. If things are going well, you can escalate from there.

If it’s a girl you’ve already gotten to know through other social situations, draw on a shared interest to inspire how to spend your date.

The important thing is to be confident, comfortable, and in control. You decide where to meet. This means you’re taking the lead and that you can choose a place where you feel comfortable (psychologically and financially). You decide when it’s time to move on to a new place. This means you maintain the alpha role (the leader) which will keep the girl stimulated and engaged. In general, too many dates involve meeting in one place and staying there — mix it up! More importantly, sweep her off her feet not by spending a lot of money, but by keeping her on her toes.

Consider the Situation

Telling the girl where and when to meet you is an easy and generally well-received way to take the leading role in the relationship. But it also means in some sense you are taking on a financial responsibility. Here’s why:

Let’s say you choose to attend a show, eat at a high-end restaurant, and then grab drinks. If you’re proposing to do all of these things, most girls will anticipate that you’ll also pick up the bill. I would not be a happy camper if a guy took me to a pricey restaurant and then told me he wasn’t paying for me. That puts me in an uncomfortable situation–I would have never agreed to go to a place so expensive if I knew that I was paying, but I also don’t want to seem like I’m just looking for free food and drinks. If you want to do something not cheap and not pay, be up front about it.

Still, it’s more likely today that a girl would be totally fine paying for herself. It really depends on the situation, so this becomes another time to ‘test’ the situation. See how she reacts when the bill comes or when you approach the cashier.

Some girls even insist on paying.  

As a college student myself, I would be more willing to pay on a date with a fellow student as opposed to one with an older, employed date.

If I were on a first date with a fellow struggling student, I would not want him to take me to a fancy place and spend more than he realistically should. The atmosphere and the prices on the menu would put more pressure on him. This pressure would leave him feeling uncomfortable and less confident, and at the end of the day, that extra money spent would have been a waste. Confidence will always win more girls than money. Since I practically live in cafes anyway, this student would have been much better off taking me for a coffee. The atmosphere and prices would lessen the pressure, and he could likely afford to pay for me. And let’s face it, paying for the girl is the more masculine thing to do.

On the other hand, when I dated a guy who worked in the financial industry and who was eight years older, I fully expected him to pay on the first date–and he did. He took me to nicer restaurants because that was where he would normally go, where he felt comfortable, and therefore, where he could feel confident.

All in all, the safest bet is to chose a place where you feel comfortable paying and pay. 🙂

Remember it’s A Two-Way Street

One thing that’s important for guys to remember is that dating is not just about making a girl like you, it’s also about finding out if you like the girl. Treat her well, but don’t bend over backwards. Trying too hard is not attractive. It shows insecurity and makes is seem like you’re overcompensating for something you lack.

If a girl doesn’t respond well to the fact that you didn’t spend a lot of money on the date or to the fact that you didn’t pay, it does not mean you failed at winning a girl, it means she failed at fitting into your lifestyle and at not being a spoiled bitch. Be glad she’s not texting you anymore.

*Important note* Most of this article assumes that you want to develop a relationship with a compatible girl. If you just want to sleep with a hot girl and don’t mind if she just likes you for your money, by all means buy her things — lots of things.

Splurge Later

You don’t have to roll out the red carpet on your first date. In fact, I advise against it.

Spending a lot is not sustainable over time and can attract a girl for the wrong reasons. If you impress a girl with your money and not your confidence and personality and then you don’t keep spending as much or even more, she’ll move on, you’ll be out whatever money you spent, and you’ll have no relationship. However, if you really hit it off with a girl, go on a few dates, and then have the more expensive date, it will make her feel really special and she’ll really appreciate it. I’m smiling just thinking about it. Do that. You’ll be glad you did.



Cece lives in Manhattan and is currently studying the social sciences at Columbia University. She offers a woman's perspective on dating and relationships.

1 Comment

  1. August 21, 2014 at 4:40 pm

    On being masculine and paying on dates.

    Sometimes I wholeheartedly pay for a date if the girls is a student, or is manifestly in a worse financial situation than I but usually I date mostly professional women who have nothing to get from me than companionship and perhaps love and affection. Then, paying for the date is an aberration and is truly sexist for both men and women as it installs an uneven balance of power. It has nothing to do with being masculine, that’s macho mumbo jumbo at best or a greed-motivated argument at worst. Young boys and girls should better be socialized to understand this, that equality of the sexes is what it says on the tin.

Leave a reply

Previous post

Coming Full Circle

Next post

What Women Want from Men - with Adam LoDolce