Dating questions answered: Should he pay on a first date?

Dating can be a minefield of questions and concerns whether you’re on a first date, a third or you haven’t even asked him out yet. That’s why we’re answering some of the most common dating questions with the help of some experts, starting with: Should he pay on a first date? Stay tuned for more questions later this month.

Man paying for date

If he pays — it’s a date

Paying for the date defines the date as an actual date, says April Masini, relationship expert behind the critically acclaimed Ask April advice column and author of four books on dating including Date Out of Your League. “If he pays for the first date, the date is clearly a date and it’s not ‘hanging out.’ This is important so that you both understand that you’re dating and not stepping into that swampland better known as the friend zone,” she explains. “When he pays for the date and picks you up, drops you off and does other things associated with dating and not hanging out, there is less confusion in the relationship.”

It happened to her: “I once went out with a guy a few times, to a bar for a few drinks and then to a movie and we each paid our own way. It turned out that this guy wasn’t actually interested in me, at least not as more than a friend. Lesson learned. I totally take into consideration whether a guy pays to make sure he’s actually into me.” Tonya, San Antonia, Texas

If he pays — he shows his financial personality

When he pays for the first date, that gives you insight into his fiscal self, notes Masini. You get to know what he’s like when it comes to spending money. “This is an important part of who he is and a great way to learn about him and to be able to decide if he’s someone you want to continue dating,” she explains. “For instance, if he insists on splitting the bill, you can expect more of the same, and less generosity than you might be looking for in a relationship. Or if he’s someone who’s toting a Groupon and a Living Social coupon and whips them both out at happy hour where your date is virtually free, he may be someone who’s always looking to cut corners.”

It happened to her: “My ex-husband was notoriously cheap. We rarely went out for dinner, vacations were unheard of unless you count his parents’ condo in Florida. Looking back, he was always tight with money, even on our first few dates where he made me split the bill every time. I should have paid better attention to that fact!” Natasha, San Jose, California

If he pays — he’s invested and wants to be there

Paying for the first date also shows he’s invested in dating and isn’t just looking for a good time (or a booty call). After all, dating is expensive. “After a guy adds up the price of dinner, the movie, the grooming expenses, the gas, the car maintenance he has to pay for to make sure he can pick you up — it’s expensive to date,” affirms Masini. “So if a guy is paying for that first date, it means he’s invested in the process. He wants to spend the money because he’s looking for a real relationship,” she explains. “Someone who’s just looking for a good time isn’t interested in investing in a first date the same way someone who springs for an impressive concert and Champagne is.”

It happened to her: “I honestly don’t mind chipping in for a date. I’m not one of those women who needs car doors opened for her or flowers every other day. But it really does feel like someone cares about the outcome of a date when they pay or at least offer to pay. It’s not the be all and end all, but it can speak volumes about how interested someone really is.” Bethany, Newark, New Jersey

More dating tips

Tips for a first date that will ensure a second date
Date disaster: Mistakes you don’t realize you’re making
A guide to letting your guard down


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