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. 12 comments.

Stir Events by Open Office Hours for all

It seems that even got the memo that sifting through online profiles and photos is a highly inefficient way to find a mate. So, they have shamelessly ripped off my “Open Office Hours” concept and introduced real-life mixer events they call “The Stir.” Curious, I signed up for my first Stir event last night in Cambridge. I figure, if Match is going to do all the work for me and set up Open Office Hours, then I’d be a fool not to go!

Before going, I did have some reservations. My biggest fear was that the venue would be full of my old Match rejects–the guys I had already dated and shot down.  After nearly a year of dating on, this is getting to be a populous demographic.  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 other.

When I first walked into the venue, I was struck by the fact that it mostly felt like going to any other bar. It was hard to tell who was there for the Match event and who was there just because their office is across the street. People were mingling, drinking, and talking.

Having gone by myself (being unable to blackmail any of the girls into accompanying me), I got myself a glass of wine at the bar and immediately realized my conundrum as a solo woman at a Stir event. You see, I’m a fervent believer in The Rules and never, under any circumstances, do I approach a man first. Normally in bars, I hang out with my girlfriends and wait for men to approach us. However, when you’re a “Solo Lurker” this is difficult. You can either sit at the bar, nursing your drink, looking lonely and pathetic, or you can grab the bull by the balls and just start talking to men yourself. Actually, the latter is pretty easy at Stir events. You already know everyone there is single and looking to meet strangers, so simply making eye contact is enough to spark a conversation with most people.

Some observations from the evening:

1. As you might expect, the girl-to-guy ratio was highly skewed.  I’d estimate there were 3-4 girls for every guy in attendance.

2. The men are all lame. And short.  (Basically, it’s a representative subsection of the pathetic male selection available online).  I did not meet a single guy who piqued my interest.  I wish I could say I was surprised.

However, the evening was not a total loss because:

3. There were some really awesome girls in attendance.  I exchanged numbers with two really friendly [straight] women and made some new friends to go out hunting for men with!

This just goes to support my growing belief that there is no shortage of amazing women in Boston, but the men are all duds.

June 19, 2012. Uncategorized. 9 comments.