Chicago Date Idea: To Pay, Or Not To Pay

Aaaaaaaaaahhh! That bit of awkwardness that seems to leave a bad aftertaste, no matter how wonderful the first date is. Paying for the bill. Who’s responsibility is it? Do you fake pump reach for that leather folder, but secretly have no intentions of paying? Do you immediately put your date in a full Nelson on the restaurant floor demanding you pay? Or are you more of a “hey thanks for picking up the tab, I’ve got the tip”.

No matter how you slice, dice or arrange it, unfortunately this can be a real deal breaker. My personal experience, coupled with various methods of research, I have decided to share my own conclusions.

1. All Men are Created Equal: No matter who did the asking, man or woman, who makes more money, BOTH parties should be prepared to foot the bill. Nothings classier than a gracious act of swooping up the check when your date forgot their wallet. Or better yet, forgot to close their tab at Butch McGuire’s the night before. Although people have the best intentions, sometimes things fall through the cracks. So be ready! It will not go unoticed.

2. Leave the Dutch Out of It: Seriously….don’t split. It’s tacky. Either you are in, or you are out.

3. Double Standard: Men should pay for the first date. Call me old fashioned, but I know millions of women that will not go for round two if the man doesn’t dish it out first. EVEN if the girl asked out the boy. Now I know there are some women that would find this old world approach appalling.  But I would bet you  know beforehand if you were taking out such an independent, strong lady such as this….so adjust accordingly.

4. Be Proactive: No, I don’t mean the skin care line. Prefacing the date beforehand relieves that sort of pressure when the waiter ends the meal. For example “Bill would you like to grab a coffee? My treat!”. Or “Debbie, I would love to take you out to dinner this evening”are both examples where you have declared you are financially responsible. A simple “would you like to go out for drinks” can leave the whole money factor looming in the air. This is an easy step to help your guest relax!

5. Gambling Not Allowed: Make your first date affordable. Don’t go over the top with a million dollar dinner, praying the other person picks it up. Save your gambling for The Horseshoe. This can help yourself relax. Remember, expensive does not equal better. Save the big spending for when you know they’re a keeper.

6. Put Your Money Where Your Mouth Is: Ladies, if you ask a man out, be prepared to pay. Yes, I know I previously mentioned men SHOULD pay.  But that does not mean they will. So think twice before where you go and what you do. If you are making the first move but don’t want to pay, chose a freebie. Take a walk on the lake, do a movie in the park or go to a free concert. If you ask, you shall receive…the bill that is.

So take my word for what it’s worth. If you disagree or have a better suggestion, I would love to hear it!