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Guys, Dating & Money: 6 Ways to Know if He’s a Charmer or a Cheapskate

By Mary Schwager, Staff

Does your man need a money make-over? Did the date you went on over the weekend create a financial faux pas?We asked our readers to send us their questions and situations where they encountered a guy who didn’t quite meet the definition of ‘classy’ when the bill arrived and asked etiquette expert, Jodi Smith from Mannersmith for some advice.

The author of this article also has a disclaimer: This article was not prompted by anyone she dated.

First question from our readers:

1. Does the man always have to pay? What’s the modern, 2010 etiquette for this? On a first date? On a second date? Okay, how about the third date?



Jodi Smith, Mannersmith:

According to modern manners, ‘the person who does the asking does the paying.’ In 2010, gender is not the deciding factor. Generally, the person who initiated the dating situation will continue to do so for the first few get-togethers. Then, if all is going well, it is expected that the other person will reciprocate in some way. So, for example, if Pat takes Christine out to some nice restaurants for dinner, by the fourth outing, Christine should be inviting Pat out for something. If Christine cannot afford a nice dinner at a restaurant, then a movie and popcorn, ice cream cones and a trip to the zoo, or coffee and a self-guided tour of the city will do. The reciprocation is not about a dollar amount, it is about taking the initiative and spending time together.

What about if  a relationship lasts past a third date. Should a woman offer to pay? What if he accepts? Check out Jodi’s suggestions.

2.  One woman found herself on a dinner date and the guy said, “You pay this time, I paid last time.” Does this show poor manners? What should a woman say to this?Jodi Smith, Mannersmith:

Yes, talk about a bait and switch. If the guy asked her out on a date then he should be paying. It shows horrific manners and she should consider herself lucky that she found out his true colors sooner rather than later. As for what to say “Oh, I’m sorry, I thought you asked me out for dinner. Here is some cash to cover my meal. If you will excuse me” as she heads for the door. Don’t look back.

Also See: Would You Date a Guy Who Is Broke?

3. Another gal says, “I can remember being invited to a college football weekend by a young man who then stuck me with my hotel bill!” What should someone do in this situation?


Jodi Smith, Mannersmith:

Darling, if you put down your credit card for the hotel room, you were paying. Consider this a swift life lesson. Be wary of weekends away with men you hardly know!

4.  A date showed up 2 hrs late for a dinner date and he had already eaten. We stopped by the closest restaurant. I ordered a drink. He wanted a water. Turns out the kitchen was closed and he didn’t have cash and he doesn’t put charges on his credit card for less than $25. I paid. We went to another place and I made sure the bill was way over $25. What should she have done in this situation?

Jodi Smith, Mannersmith:

No gentleman arrives two hours late for a dinner date, already full, for a woman he is trying to impress. If he called to say he would be two hours late, you say “I am so sorry tonight won’t work” and wait to see if he asks for another date on another night. Plus, if the restaurant’s kitchen was closed, I shudder to think what time it really was… At first I thought the restaurant did not put through charges of less than $25, but it was this joker’s own personal policy. As the Sex in The City girls would say, “he is just not that into you.” This sounds more and more like a booty call. If you are fine with that, so be it. If you are looking for a keeper, keep looking.

Also See: What Married Men REALLY Talk About

5. Here’s a kicker, one woman’s short term boyfriend always complained he was broke. Then one night she discovered him calling his bookie from the restaurant to make a bet. What would a classy gal say and do in this situation?


Jodi Smith, Mannersmith:

If she loved him, it is GA (Gamblers Anonymous) for him. No more paying for his attentions. If he wants to see her, he needs to plan and pay for some of their dates. If she was just dating him, it is a safe bet that it is time to move on.

6. And we got this one from a male reader. I proudly marched into my hometown restaurant, proceeded to go on and on about great it was to be there again… and forgot it was cash only! My date had to pay, which she graciously did, but I felt like a heel!! Should a woman give a guy another try in this case?

Jodi Smith, Mannersmith:

Dating faux pas such as these make great fodder for wedding day toasts. A great guy takes this understanding gal to one of the best restaurants in town, remembers his wallet and pays for the whole thing.

We want to hear from you — Have you ever dated a cheapskate? Does it matter to you whether a guy pays or not? Leave us a comment!

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