Dear Ella,

I’ve recently stepped up my search for a serious relationship. I have a profile on JDate and have gone on a few blind dates. I’m pretty good at first date stuff like small talk and where to go, but I’m constantly stumped by paying etiquette.

Being kind of an old-fashioned guy, I like to pay on the first date, but it’s the subsequent dates that I’m having trouble with. I’m just out of university and building my career. I can’t afford to be spending tons of money on dating. Even a basic dinner is often more than $50, and the same goes for a movie date.

I’m very uncomfortable asking my date to pay her way. Sometimes they offer and sometimes not, but when they do offer, I feel like a “schnorrer” taking their money. Once I went out with a girl who insisted on paying her  own way on the first date, and that threw me right off. “If I pay then we are on equal ground,” she said. I actually understood that.

Is there a right way to handle this?

Paying Perils

Dear Paying Perils,

Much depends on where and how the date originated. If you met for the first time on JDate, then you’re probably not going to a movie or dinner. My guess is you’re going for coffee or drinks. You didn’t invite her, and she didn’t invite you. It’s a mutual decision to meet, and usually you each pay for yourselves. If you like her and ask her out again, that will be your first date, and you should pay.

When you ask a girl out, it’s your invitation so it’s up to you to pick up the tab. On the second date, do something a little less expensive like go for a bike ride or a walk in the park. Maybe stop for some ice cream. See if she offers to pay. By the third or fourth date, she should be dipping into her wallet.

There’s a subtlety in the way you approach things. For example, if you go to a movie, you might pay for the tickets and say something like, “How about you pick up the popcorn and drinks?” That’s a more natural and comfortable way than buying your own ticket while she buys her own.

Don’t let money be the elephant in the room. The whole point of dating is to get to know each other. The way the two of you handle money is very much a part of your personalities. You certainly don’t want to come off as a tightwad, but you don’t want her to feel like you are overpowering and controlling, either.

Believe it or not, in most situations, it will work itself out fairly easily. Don’t keep a balance sheet. You need to be socially intelligent. On a first date, she’s judging you on everything: your clothes, your manners, your looks, your personality, your intelligence – just like you’re doing with her. There’s enough to be aware of without letting this part get in the way of what might bloom into a great relationship.

Think of dating as an investment in your future. Once you have a few dates with the same person, you can actually broach the subject directly if necessary. Treat each other with respect and sensitivity. In the meantime, enjoy the excitement of getting to know the new woman in your life.

Readers may submit their questions to Ella at The CJN, e-mail: [email protected]. But Ella is not a professional counsellor. She brings to the questions posed by readers her unique brand of earthy wisdom. Her advice is not a replacement for medical, legal or any other advice. For serious problems, consult a professional.