Dating for Dummies

So you want to ask me out on a date. Great. I’d like to take a few minutes and give you a few pointers on how NOT to screw it up. It’s really not THAT complicated…

I recently went on a date with a guy that started off fine, but then went way south (and not in a good way either). Please learn from his mistakes.


First and foremost, I should probably warn you: I’m a judgmental bitch. Be original because I’m more than likely going to judge you based on how creative you are with planning a date. When you suggest dinner at your favorite wing spot, games, and fireworks, you’re definitely off to a great start.

Your favorite wing spot should never be Hooters. We are gay men. I do not want to be eye level with some girl’s fake knockers. 

If YOU are asking ME out on a date, expect to pick up the check. I am not saying I’m opposed to paying the bill at the end of the night, but if it was your idea to set this all up, do not look at me awkwardly and wait for me to pull my Visa out at the end of the not-so-delightfully tacky and unrefined dinner to split the bill.

If you say we’re going to go to Dave & Busters to play games, do not go back on your word because “there’s a chance we’ll miss the fireworks.” I’d much rather be playing Whack-a-Mole or Pound the Beaver than staring at the sky for 15 minutes wondering how much money the city just spent to shoot off some colorful explosives. If you play your cards right, we could make our own fireworks later.

If you deny me the joy of playing games because we’d be running late for the fireworks, stopping for a drink at your favorite rooftop bar is acceptable. What is NOT acceptable however is taking me to said rooftop bar and complaining that two drinks just cost you $32 plus a tip. If it’s really your favorite rooftop bar (that you say you come to all the time with your girlfriends) then you should be fully cognizant of the fact that their drinks cost this much.

Let me sip my drink while I’m out on the roof. Do not rush me and make me chug your $16 cocktail so we can get to the fireworks. If you didn’t think we were going to have enough time, we should have stopped at Walgreens and bought a bottle of wine and Solo cups. I’d be just as happy. Plus it’d be more creative – refer to Lesson 1.

Do not, I repeat DO NOT, try to make out with me at Navy Pier after only having known me (the week that we spent chatting on Grindr and by text don’t count) for three hours. If the fact that I keep repositioning my stance so you’re forced to remove your hand from my back pocket or from around my waist doesn’t tell you that I’m not really feeling this date at this point, then you really need to brush up on your dating skills. Besides, I am not a fan of PDA to begin with, let alone after three awkward hours of eating chicken wings and chugging one drink. Try again after six and we’ll see what happens, but at least then I can blame my impaired judgement.

Stop trying to hold my hand every 30 seconds walking back to Michigan Avenue to catch the bus. Also do not keep trying to be touchy-feely once we’re on the bus. Please reference Lesson 7. We are not a couple, and – at the rate you’re going – we never will be.

Try to carry a conversation. I’m sure you’ve realized at this point in the night that the date is not going to end up with me back in your bed, but at least don’t make things even more awkward by sitting in silence.

Reread this list. Study up. Make flash cards. Do whatever you need to. Just don’t be an idiot like this guy. If you are, you will definitely not get a second date.

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