Money for Men: First date advice

Going on a first date is certainly not easy. You have to worry about keeping the conversation moving, your dinner off your shirt, and your eyes from staring at her cleavage. It is truly a hard knock life for guys! To make matters worse, there are certain money questions that can often complicate, or even ruin a first date.
Where should you go?
There is a school of thought out there that you should take a first date to a fancy and expensive restaurant. This theory is based on the belief that there is no better way to impress a woman, than to wine and dine her at your local trendy hot spot. If your intentions with this woman are purely, let’s say short term, then yes, this maneuver might actually work. However, if you are actually looking for a longer relationship, this is actually a boneheaded move. Going to a four star establishment may score some points in the financial solvency category, but you have to do some forward thinking here. What will happen to this image when you bring her to Applebee’s on your second date? Unless you can continue to afford to bring her to a restaurant in that price range again and again, then stick to a more moderately-priced restaurant.
Coupons and Tipping
Although I am usually all about saving money, when it comes to a first date, I would leave the coupons at home. Yes, being money savvy is a characteristic that most women will admire. Still, you don’t want her to think that her every purchase will be closely scrutinized and that she will end up starring in an episode of Extreme Couponing. In addition, the usage of coupons on a first date could incorrectly indicate to your date that you have more financial problems then the owners of the Dodgers and Mets. Good luck overcoming that impression unless you have ties to the royal family of Genovia or another exotic location.
As for tipping, no manner how bad the service is, be sure to take care of your waitperson. I had a friend who had to wait in a hospital waiting room for 12 hours straight and the only reading material available was a stack of women’s magazines. He reported that almost every single issue had an article about how you should ditch a guy who leaves a bad tip.
Who Actually Pays for the Date?
There have literally been millions of articles that have debated this age old question. Luckily for you, I have an easy way for you to determine the answer. During a heterosexual date, when the check comes, simply reach into the front of your pants. If you can locate a penis, then you are responsible for paying. Yes, it is nice when a woman offers to pay, or even split the check, but when the bill comes, man up and take out your wallet.
Yes, I know the year is 2011 and there is a solid chance that your date might make more money than you do. Despite these facts, I still think you should confidently insist that you take care of the bill. And besides, it’s what Chuck Norris would do!
Money Talk During the Date
I want you to try something new here. Instead of trying to think of the next story that you are going to tell your date about saving a neighbor’s kitten, try to actually listen to what she is saying. Listen for clues that she might not be that great in the money management department. Consider how hot your first date would have to be for you to pursue a (real, not “short term”) relationship if she casually blurts out that she is sick of her credit card companies calling her every day over her $65,000 debt. How about if she seems to have a inordinate amount of spare time since she has been unemployed for the last year and a half? Even if these might not be deal breakers for you, it is certainly nice to know what you are getting into.
Likewise, if you have some financial skeletons in your closet, it is not mandatory for you to air them out on the first date. Also, if you are currently without a job, try to come across upbeat about getting a job in the very near future. Even if you claim to be a charter member of the Oprah book club, you are not going to score a second date if she thinks you have no prospects of ever being employed.

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