Dating Dealbreaker: The Cheapskate

I may still not entirely know what I’m looking for in a man, but over my years of dating, I have discovered a lot of things I’m definitely NOT looking for!  And so, as a public service to men everywhere, I’m going to share what some of those Dating Dealbreakers are.  Today’s installment is about the dreaded Cheapskate.

First, let’s lay out some ground rules.  Who pays for the date, anyway?  I’m rather old-fashioned, and I believe that whoever asks for the date should pay.  As a Rules Girl, I never ask men out on dates, and therefore THE MAN SHOULD ALWAYS PAY.  Period.  I will always offer to pay half and halfheartedly reach for my wallet, but if the man actually takes me up on my offer, then God help him.  If we split the check on the first date, I’m actually pretty cool with that and will chalk it up to “Well I guess he didn’t like me that much.”  If he asks me out again after that, I might give him another chance, but if splitting the check becomes a pattern, then that’s a dealbreaker.

Why?  Well, splitting the check is a big red flag that the guy is probably just a cheapskate in general.  And nobody likes a cheapskate.  If you continue to date this dude, you can look forward to lots of cheap dates and squabbling over amounts (“I had a slice of cheese pizza, but you had the pepperoni, so you owe an extra 50 cents.”)  On your honeymoon, you’ll probably find yourself strapped to the top of a bus in India, since the air-conditioned compartment was “too expensive” at $2.  And once you have kids, well, snaggle-toothed little Jenny doesn’t really need those braces, anyway.  (“Do you think money grows on trees?”)

They say that money troubles are the #1 cause of divorce, so it’s important to find a guy with similar financial values to your own.  As for me, I’m generally responsible with money and save for the future, but at the same time, I do enjoy the finer things in life and am willing to pay for them.  So, I need a guy who does too.  That’s why I’m always on the lookout for:

Top Red Flags that the dude is a cheapskate:

1.  Splitting the check.  Or (worse) letting the girl pick up the tab.  The man should always pay for the first 10 dates–up until the point when you’re in an official relationship, and then it’s fine to begin to split things more evenly.  But during the courtship process, the man needs to be the man and pick up the damn check.  No exceptions.

2.  Complaining about how much things cost.  I know, it’s ridiculous that cocktails are $18 here.  But you picked the place, and I don’t want to hear a word of complaint about how much anything costs on the date.  Major turnoff.

3.  Picking cheap dates.  This one is tricky because since the man is paying, he obviously should pick only dates that he can afford.  And actually, some of the funnest dates I’ve ever been on cost next to nothing.  A picnic in the park is ultra cheap and a great romantic date.  What I’m talking about here as the red flag, though, are the dudes who always want to meet for “drinks” without ever buying you dinner.  Presumably because dinner is too expensive, and really he’s just trying to get you drunk, anyway.  We’re onto you, cheapskates.

At this point, I’m sure the men reading this blog are annoyed (“Is she just looking for a free meal ticket?”)  The answer is no.  I have a job and my own money and am perfectly capable of taking care of myself.  But, it’s nice to let a guy take care of me for the evening.  It’s a test run for the whole relationship: how does it feel to let this guy take care of me?  That’s really the whole point of the dating process, isn’t it?

There’s probably an evolutionary component to all this–i.e., women are looking for providers for themselves and their children.  I have a male friend who says he makes a point of always buying dinner for a woman on a date.  “Feeding a woman makes her trust you,” he says.  Something to keep in mind, boys, the next time you’re tempted to split the check.

June 26, 2012. Dating Dealbreakers.


  1. Pedro replied:

    I almost always make a point to pay on the first date . . . but 10 dates in? I don’t think so honey! Look forward to hearing more of your deal-breakers (though really, I’d try to concentrate more on what you ARE looking for :p )

  2. Stir Events by Open Office Hours for all « stilettosoncobblestone replied:

    […] Luckily, this fear turned out to be mostly unfounded: I only ran into one guy I knew–the cheapskate known as the Guy Who Splits the Check.  We pretended not to know each […]

  3. jeff replied:

    Seriously? I get it if a guy complains of the cost or takes you to a dump, but if you equate a guy paying for everything with respect or attraction, then your views are seriously skewed. Respect or attraction should be found in the interaction. Different people show care and respect in different ways. I would recommend checking out “the Five Love Languages” over the Rules.

    Also, having the same monetary values should not equate with “he pays for everything.” Just from a financial responsibility stand point it doesn’t make sense for the guy. If a guy goes on a few dates a week it really adds up. Plus you want to avoid the high maintenance girl. Btw, getting drinks often costs more than just getting dinner. But its alot less pressure, lets you cut your losses earlier on a bad date, and allows for flexibility.

  4. Adam replied:

    LOL- As a guy, the only way I’ll give a girl a pass on offering to pay half is if she has some extenuating circumstances, such as being a full-time-student, or if she offers something like “I’ll pay next time”. If she doesn’t offer, I’m FAR less likely to be interested in her (although I’d probably be interested if I were just looking for a lay). A woman who willingly pays her share means she is interested in ME, rather than what I can do for he,r and is probably the kind of modern-pragmatic-feminist woman who’s looking for a partner, rather than a gold-digger materialist looking for a provider to mooch off of.

    And judging the date on how much he spends!? How petty. Last Friday, I took out an attractive and intelligent girl, made up what we were doing as we went along, and I spent a total of about $10, including gas (I picked up the ENTIRE tab though). She said it was by far the most romantic evening she has ever had, and if you heard the details you’d probably agree.

    Based on your list of dealbreakers, “petty materialistic gold-digger” is the kind of woman you are. Are you incapable of supporting yourself? Good luck in your quest of finding a desperate schmuck and guys just looking for a lay There are plenty out there.

  5. chris replied:

    calling a man cheap just because he doesn’t spend what you think he should is shallow, immature, and just plain dumb, it shows that your only concern is how much money he can spend, you say you have money so why are you bringing him down because he’s being careful with his, money spent should be on someone that wants to be with you regardless of how much or little money you spend

    • Daphne Reese replied:

      It isn’t really about the amount of money being spent (like I said, some of the best dates are cheap/free, such as outdoor picnics). It’s all about the attitude. There’s nothing wrong with being frugal or careful with money. The problem arises when people cross the line into being miserly Scrooges (as in, always depriving themselves and the people they love, just to save another penny). It’s a lifestyle choice, really, and these Scrooges would be happiest with a fellow Scrooge, happily clipping coupons and staying home eating dollar-store spaghetti for the rest of their lives. That’s not me.

      Although I do try to be careful with money, I definitely enjoy the fine things in life and I’m willing to pay for them. I need a partner who feels the same way as I do about money. That’s why I’m always on the lookout for The Cheapskate on dates. Most people are on their best behavior in the early stages of dating, and if a guy balks at buying me $6 popcorn at the movies, then it does not bode well for our future together.

  6. Wendy W. replied:

    I personally applaud you for writing this article. I’m not sure what happened to men over the past few years but it seems that they are far too comfortable with not stepping up to the plate as far as treating a woman well. I think it may have something to do with the feminist movement but it also goes along with women seemingly having very little respect for themselves evidenced by their quickness to go to bed with a man or to be disrespected by men. Just look at all the reality shows and pornographic parephernalia. Women need to take a long, hard look at themselves and where we’ve landed just in the last 25 years. I, personally, expect a man to pay for most dates and I won’t even entertain the idea of splitting a check until we are living together or engaged to be married. Men need to grow up and learn how to be providers as their forefathers did and stop whining like children that we aren’t picking up enough slack. Women need to feel secure and taken care of, the ones with self respect anyway. The rest have serious issues and probably have nothing to offer aside from their half of the bill if they are willing to settle for that level of treatment by a man. Just a thought.

  7. Marisa Chauncey replied:


    Sounds like you have some serious issues with women and maybe have been taken advantage by someone in the past. Also, the fact that you would be okay with sleeping with a woman and possibly leading her on just speaks to your character. I hope this “intelligent” woman that you have met sees through your veneer to the “real” you.

    • vlad replied:

      Good successful women would not expect to be taken care of as they can take care of themselves, they look for a partner not a sugar daddy. As a guy I want to be with someone that wants to be with me, not with someone that is looking to benefit from my possessions.

      Obviously the author doesn’t believe in equality between a man and a woman. So what exactly does she bring to the table? What is the guy getting out of it? She is suggesting that man are beneath her and we need to pay for the privilege of spending time with her.
      Good luck finding a good man.

  8. Paul Wacker replied:

    Wendy, oh Wendy…self entitled princess are we? Daddy’s little girl deserves nothing but the best, eh?

  9. Carol Steele replied:

    Well, Im dating a man in his late 50;s. Im older than him, but look younger. The first time I asked him out. Nice place, a little pricey, but I paid for everything, because, I asked him. He owns lots of rental property and has enough money, He asked me to dinner, I told him where I wanted to go. Not That expensive!! He said, ” can we go dutch”, I said, No, please don’t be a cheapskate. He has never taken me out and paid for it so far. But, he gets sex as well, which I like, but what the hell….C

  10. moon replied:

    if they are NOT taking me out on a “real” date by the third time asking me out, I pass on them. now they find free things to do and call it “hanging out”….going for walks, free museums, etc. lmao. and they expect a make out session with that same crap I can do with a girlfriend or my dog??? lol. no wonder men are turning more to porn and prostitutes.

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