The Only 4 Dates You’ll Ever Go On

As I turn my head and look backwards, I see the early days of my twenties when I was running around in togas and saran wrap (yeah, I had a good time in college) and the most romantic thing that happened was when a guy washed off the ping pong ball before sinking the next shot. I mean really, if that doesn’t make you swoon, I don’t know what will.

Now that I’m officially in my “mid-to-late twenties” I actually have to start dating. Awkward conversations; leaving dinners hungry because you can’t chow down on tots and cupcakes (I have a very sophisticated palette); worrying about your outfit, your hair, and if your shoes leave you a respectable number of inches shorter than your date – it’s exhausting. So between me, my friends and friends of friends; I’ve collected lots of dating stories and have realized you’re probably only going to go on 4 types of dates. So prepare yourself… here’s how I break it down:

1) The Training Wheels Date – come on, you know this guy. You don’t really like him. He’s a little boring. You have next to nothing in common with him. But it’s been awhile since you’ve been on a date. Maybe you’re just out of relationship and you’re feeling like it’s time you finally went out with a guy again. You need to get back into the groove, master the witty banter, remember how to stop after 2 drinks and that you don’t need to have dessert after every meal. This is where Training Wheels comes in. He’ll help you get used to being back in the dating circuit. It doesn’t matter if he likes you, or if you go on more than one date. This one’s really just about the act of dating and not about the person.

Life Span: 2, maybe 3 dates. Tops. Training Wheels is probably a nice guy. He’ll probably pick up the bill (though you’ll make the grab, of course). He’s polite. But unless he’s dumb enough to keep trying when there’s obviously nothing there, you’ll send a polite “thanks for dinner” text and never speak again. Time for the 2-wheeler.

2) The “One of you likes the other one more” Date – this never ends well. This is the type of dating situation where it’s clear one of you is more into the “relationship” than the other. This person will always pay, will always text/call/email first and will always be available and forgiving when the other person bails on plans. They probably sent a relationship request on Facebook. This person will try to bring up the “what are we doing with this relationship?” conversation while the other person really just wants someone to hang out with during the week and someone to sleep with after the bar closes on the weekend.

Life Span: 3 – 6 months, max. Or really, however long it takes the less interested party to find someone to replace the more interested party. They’ll keep them around while it’s convenient and uncomplicated. It’ll never last more than 6 months though. Because no matter when you start your relationship, by 6 months you’ve hit one of two major milestones: 1) the holidays and only one of you bought the other one a present – or – 2) summer approaches and you’re not splitting a timeshare.

3) The “OMG He Finally Asked Me Out!!!!!” Date – Don’t get too excited that dream boy finally asked you out. He probably heard you liked him and knew you’d say yes (and hoped you’d put out). Now to be clear, this is not the guy you’ve been playfully flirting with and finally decided to go out with. That guy generally exists only in movies and poorly scripted TV shows. This is the guy you’ve been fawning over, you’ve been telling your friends about him, and you’ve been telling your mutual friends about him. You probably decided to wear your skankiest outfit on the date. You probably let him get you drunk and then made a series of bad decisions. You will also probably never hear from him again.

Life Span: 5 minutes after you sleep with him

4) The “Hmmm, I Might Like This One” Date – is it love at first site? Probably not. But he’s kind of funny, kind of cute in a quirky way and surprise of surprises there are none of those awkward pauses while you’re out. He also insists you split dessert and lets you have the last bite. Or maybe that’s just my version of this guy.

Life Span: This one’s a keeper.

So who out there’s been on one of these 4 dates? What are your dating horror stories , or (ok, I guess) success stories. Did I leave any dates off the list? I’m hoping for lots of comments on this one, ladies!


Posted on June 15, 2011, in dating and tagged , , , , . Bookmark the permalink. 5 Comments.

  1. I’m on date #2 with a #1, and I hope it turns into a #4! Awesome post!!!

  2. Good luck! I can dish all about my #1s who didn’t turn into #4s. Fingers crossed for you 🙂

  3. I’ve experienced all but the #3s!!! Yes, I am a good girl 🙂

  4. Hehehe, Cara… you’re too funny. We can discuss which number Mike was 🙂

  5. “the most romantic thing that happened was when a guy washed off the ping pong ball before sinking the next shot.”


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