5 Cheapskate Conundrums: Is It OK to Use a Coupon on a Date?

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Also: How do you avoid getting ripped off if you’re the world’s worst, most timid, most undemanding haggler? People concerned (obsessed?) with saving money have issues, such as …
Is it tacky or thrifty to use a coupon on a first date?
Seems to me like this is always an undeniably thrifty move, so this isn’t necessarily an either/or proposition. Whether you think the first date (or any date) coupon is tacky or not is a different matter. Anyway, Ask Coupon Sherpa asked readers to weigh in on the matter, and women were nearly twice as likely as men to vote “tacky” rather than “thrifty.” How come? Some insight why:

For example, 30-year-old Maisie, a married professional and survey participant, interpreted it as a guy slyly claiming, “You’re not worth the full price of dinner.”

But what if your new beau is already trying to save up for your engagement ring? You’re only making it harder on the poor guy.

Anyway, Groupon, the group-buying site that started in Chicago and that’s spread like wildfire, is trying to make the practice of first-date couponing seem a lot less stingy and more romantic. How is the service trying to change the coupon’s tightwad image? By—get this—offering college scholarships to kids born to parents who used a Groupon on their first date. Such Groupon babies are being dubbed Grouspawn. The idea may sound icky, as does the name — which to me sounds like something you’d see on the menu of a trendy restaurant. “I’ll have the grilled Grouspawn with a side of roasted potatoes.”

Is this for real? Who knows. But perhaps Groupon can succeed where other cheapies have failed in getting rid of the stigma attached to coupon-dating. The site has even started a dating service, and—surprise!—almost all of the members are guys.

But let’s think about this for a sec. Using a coupon on the first date may be an indication that a gentleman is not one to blow his money quickly and heedlessly all in order to impress a young lady into doing something she’ll regret. Perhaps using a coupon is a sign that he wants you, like his money, to be around for the long haul. Perhaps using a coupon is a sign that he can put off instant gratification, and that he can commit to something. Then again, maybe he’s just a cheap bastard and will always be so.

On to the next issue …

What do you do if your boyfriend is so cheap he makes you pay him back for a postage stamp?
This seems like more of a problem than a first-date couponer. This seems like somebody who doesn’t know how to share, and that doesn’t work in a long-term relationship. The question comes up in Salon’s “Since You Asked” column, and here’s a snippet of the advice given:

Try this. Take his wallet and look in it for dollars. Ask him if you can have a dollar. Look at his money. See how much he has. Does he panic? See what happens if you open his wallet and take some money out of it and say to him, Can I have this?

Is it OK to break up with somebody because they have too much debt?
A recent NY Times story dwells on this topic, as well as other questions such as: At what point in a relationship do you have to disclose that, say, you have $30K in credit card debt and $59K in student loans? Also this sticky issue:

If one person brings a huge debt to a relationship, who is ultimately responsible for making good on the obligation? And if it’s $170,000, isn’t the more solvent partner going to resent that debt over time no matter how early the disclosure comes? After all, it will profoundly affect every financial decision, from buying a home to how many children to have.

Should I cut my lawn guy?
This is one posed by the Atlanta Journal-Constitution’s Bargain Hunter. Her regular lawn guy charges her $40 to mow the lawn. But an entrepreneurial young man in her neighborhood recently approached her and said he’d cut the lawn for $7. What’s the ethical, financially responsible, and smartest move here?

What do you do if you’re the world’s worst, most timid, most undemanding haggler?
How do you manage the painful process of buying a car, for example, without getting ripped off? A post at The Simple Dollar offers a solution, by way of a reader who knew she wanted a certain car at a certain price, but feared that she’d be bullied into overpaying at the dealership.

What did she do? She asked two of her friends known for driving hard bargains to get her a better deal than she could have gotten herself—and then she gave them the difference as a thank you. The difference wound up being $1,200, and her friends didn’t accept the full amount. So all in all, everybody—everybody except people working at the car dealership—won, especially the woman who wound up with a new car to drive:

All I did was show up at the dealership, sign a paper, write a check, and walk out with the keys… I might not have gotten the best deal, but it wasn’t anything worse than I would have negotiated for myself. I didn’t feel awful about the purchase and the extra money went to my friends instead of to the dealership and I didn’t have to spend weeks hunting for the right model.