Worst. Date. Ever.

February 13, 2009

Valentine’s Day is upon us. That means that many of us will be giving gifts, or going on special dates. Some of us will be hoping for a first date with someone. Others will be planning a date with a spouse of many years. Some dates will be magical, others ordinary and a select few will be awful. The rest of us will skip Valentine’s Day, because we give up.

So I’ve got some advice to keep your Valentine’s date from being a total failure. Whether you’ve been married a long time or are heading out for a first date, there’s some advice that bears mentioning to everyone, because some of us are forgetful. Or just insensitive jerks.

Just so you know, I was a huge ladies man before I got married, which the ultimate show of being a ladies man. I mean, I liked ladies. I even spoke to a few. But I did have enough dates to have gone through some lousy dates. And it’s always fun to learn from our failures…or our dates’ failures, which is what I’ve done here. At the end, you can share your advice or worst date stories!

Now, I’ve worded this as a guy who dated girls, but if you’re a girl, the advice still goes.

Good Idea/Bad Idea: Going on a Date

Good Idea: Double Dates
Hey, double dates are fun. They ease the pressure for two new acquaintances. For married couples, they’re a fun way to share an evening with friends. Conversation and laughs often flow easier when four people are involved.

Bad Idea: Tricycle Dates (Double Dates Minus One)
It’s not a good sign when the other guy (or girl) doesn’t show up. Now I know what you’re thinking. I tell you I had a date with two sweet ladies. ‘What’s the problem, Matt? I don’t see a problem. Sounds like you’re my new hero.’ Well let me tell you, nothing turns the second lady into a mumbly third wheel faster than being spurned by her date. If you show up to a double date and there’s just one person joining you, sit your date down with the other lady and suggest a ‘girl’s night;’ then run out of there! You cannot salvage the evening for you and your date. You cannot switch off and date the other girl for half the night. You don’t have it in you. If only I could go back and tell young me that advice that fateful night.

Good Idea: Flowers
Gifts of all kinds are awesome. Everyone likes presents. For some reason, girls like flowers. Gifts are a fun and unique way to show affection.

Bad Idea: Gas Station Flowers
I lump all bad gift giving into the category of ‘gas station flowers.’ Flowers are naturally a good gift. Flowers from a gas station are naturally an insensitive, crappy gift. There are all kinds of ‘gas station gifts.’ I don’t mean to tell you I’ve learned lessons from my bad gift giving. I mean I’ve been given some pretty lousy gifts. I didn’t think girls could be bad gift-givers. I’ve gotten thoughtless gifts, unwrapped gifts tossed in my lap, even re-gifts. From girls who are supposed to like me! Nothing tells your sweetie you care like some costume jewelry with the ‘Walgreen’s Drug Store’ sticker still on it. Gee thanks, can I go home now?

Girl: Here, happy birthday. (Toss gift into lap)

Me: Why thank you, it’s a DVD movie!

Girl: Yeah, I didn’t have time to wrap it. I fell asleep earlier.

Me: Well!…That’s…okay. Better for the environment.

Girl: You think I could get a neck rub? I kind of slept on it funny.

Me: …But it’s…my birthday.

Girl: *inscrutable staring*

Me: …Well, I’m going to go home and watch my movie now, since all my other friends already have plans for the night.

Good Idea: Seeing a Movie
Seeing a movie has to be one of the most popular date nights in America. They’re fun, cheap, and they minimize the amount of talking to be done between nervous first-daters. They also minimize the amount of talking to be done between married people who have nothing more to say!

Bad Idea: Being Blindsided by a Movie
Guys, I cannot stress this enough. If you plan to take a girl to a movie, especially on your first date, go to the theater, plunk down $8 and see the movie the night before. I know, sounds ridiculous. But, you can read the reviews; you can check the rating. But if you do not preview it, they will sneak something into that movie, just to embarass you. Something sleazy or weird or naked. Suddenly your hand starts to sweat as you hold your date’s hand. She starts to squirm as she projects her discomfort with the movie into discomfort with you. She unconsciously believes that because you selected this movie, you want her to do whatever it is that lady in the movie is doing. Or worse, she thinks you already do whatever it is they’re doing. And whatever it is, you don’t want your post-movie conversation to steer toward that awful subject. Just doesn’t prime the night for a good ending.

Good Idea: Discussing Your Faith
Often, it’s a good idea to discuss things that are important to you with your date. Faith is inevitable to come up soon enough.

Bad Idea: Discussing Your Faith
Depends on how much you want a second date. It’ll either make or break you, and you can’t always predict it. Some girls go all soft and mushy when you tell them you’re a youth pastor. That’s how I snagged my woman. Some women look at you like you have ‘POOR’ written in big letters on your face. Girls, this can backfire on you too. You don’t want your date to realize he’s suddenly on a tricycle date with you and Jesus.

Note: Especially do not discuss faith while on a tricycle date…with the girl who’s not your date…while your date says nothing and does not even feign interest.

On the one hand, that date ended at about 5:45, a personal record. On the other hand, I saved lots of money by only going on half a date and had plenty of time afterward to catch a movie with my bros.

What’s your best dating advice, married or unmarried? Worst date stories the rest of us can learn from?