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Dating bucket lists: Dinner and a movie to a threesome

What's on your dating bucket list?

What's on your dating bucket list? Photo Credit: iStock

A "bucket list" refers to things you want to do before you die, or, "kick the bucket." In this particular setting, kicking the bucket is diving into a relationship, because, for all intents and purposes, your dating and sexual career is pretty much dead.

Do not go gentle into that good night. Make a bucket list of your own and see it through. Here are the experiences we consider musts before you settle down.




The One That Gives You A Story

Every girl needs to have at least one horrible dating experience under her belt. And lucky for us, we usually end up with far more. Fun! Horrible can mean a lot of things in the context of dating. It could mean a complete lack of chemistry, or it could mean you found yourself sitting across from a guy who measures his self-worth by the number of retweets he gets in a day. Or maybe he drinks too much and you end up with a front row seat to the vomit show. Once again, fun! Sure, this list sounds very bad and imagining yourself in any of these situations makes you want to die a bit, but there's a silver lining: The Story.

No one wants to hear how amazing your most recent date went or how perfect the guy was. If you insist on this, know that on the outside your friends are saying, "That's so great! Wow, you really deserve this." But on the inside, "GFY, GFY GFY," has become a mantra of some sort. (Hint: That's not short for "good for you.")

Instead, people want to hear about the time your date took you to Union Pool in Brooklyn on a Saturday night because he "heard good things." They want to hear about the time you and your date sat in complete silence for 15 minutes watching an "SNL" rerun playing on the TV above the bar, and how he still expected you to go home with him (in my defense, Drake was hosting and it was very funny). Rarely will a date ruin your life, so you might as well embrace it, blog out it, and tweet about it... I recommend all of the above.

The One Where No One Drinks

Imagine this: Meeting a complete stranger who has expressed initial interest in your looks and personality, and vice-versa. Think about how nervous you are and how you're over-thinking every decision. Black jeans or dark greye  Hair up or downo When do I need to leave my apartment in order to arrive exactly four minutes latea You know, the important questions. Now imagine sitting across from this stranger, anxiety, nausea and all, and you're both completely sober. A modern horror story.

I'm a very anxious person to begin with, even around my own family. And first dates don't do much to calm these feelings. There's a lot of, "Oh my god, oh my god, oh my god, oh my fricken god" going on in my mind. This is why my preferred setting for a first date is a bar, so imagine my reaction when a guy suggests meeting for coffee at two in the afternoon.

Even so, these dates are necessary and force you to stray a bit from your comfort zone (read: dimly lit bar). These dates also act as a sort of check-up on my social skills. It's amazing how much faster conversation topics come to my mind with the help of gin compared to an iced coffee, but this is something I'm working on. It's called personal growth, or something dumb like that.

The One With Dinner And A Movie

Dinner and a movie has become a dating cliché, so much so that people are now adverse to the "traditional" format. Therefore, dinner and a movie has practically gone extinct in New York, and this make me sad. Call me old fashioned, but if a guy asked me out to dinner and a movie, I just might drop dead from shock. It's always, "Let's meet up for a drink," which is fine, but there's something so nice about the idea of dinner and a movie.

I recently went to the movies with a guy for our third date, and even though it was only half of the magic formula, it was already better than previous dates. I could only imagine how much better it would have been with dinner! Full disclosure, we saw "The Entourage Movie," but I swear it was done ironically and I didn't laugh (I laughed).

In summary, guys, the next time you're asking a girl (me) out, make it dinner and a movie. They (I) will be so excited and appreciate the time and effort you put into planning your (our) date.




The One Who Gets You Out Of Your Comfort Zone

If you have a "type" of girl that you're always attracted to, try the opposite. For me, my type is any girl with a pulse and boobs, so the opposite of that leads to necrophilia and a story I don't want to write about here. But back to you. Try something new. If you always go out with blondes, try going on a date with a brunette or a redhead. If you always go out with girls of one race or ethnicity, please, branch out. When you go to an ice cream parlor, eating the same flavor every time starts to get old. We're in New York City. It's the largest ice cream parlor in the world. Try as many flavors as humanly possible and you'll find something you never knew you liked.

The One Night Stand

I talk to a lot of guys who have never had a one-night stand -- OK, not a lot, but more than there should be -- and that is just baffling to me. For girls, I understand there's a certain stigma attached to a one-night stand, but guys, you're missing out big time if you've never indulged. One-night stands are meant to be nothing but fun. There are no strings attached. You don't have to wake up the next morning after an evening of pure filth and feel ashamed because you have to go run errands with the person you were just sexually degrading eight hours earlier. For the record, ladies, that stigma is garbage.

The One With The Threesome

I've never met a guy who didn't want to have a threesome, and I'm not different. I so badly want to have a threesome before I shackle myself to someone for the rest of my life. When I say "threesome," I mean two girls and me; not me, some girl and Christian Grey -- that isn't going to happen. A threesome isn't an easy subject to broach, but if you stumble upon a fairly sexually enlightened gal, find a way to bring it up and see how it goes. What's the worst that could happenh Like Wayne Gretzky said, "You miss 100 percent of the shots you never take." On a personal note, I was very recently propositioned for a threesome with two very attractive girls, but declined because I thought it might end with me being held at gunpoint. Remember, safety first. But that's a story for another day.

Head to every Friday, as Matthew and Kelly take on the realities of dating in NYC from both sexes' points of view. To inquire about NYC dating advice, email them at Your question may appear in a future column, but no names will be used.


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