Ask Drew: Date Ideas He’ll Actually Like (And Hate)

“Let's face it: a date is a job interview that lasts all night. The only difference between a date and a job interview is: not many job interviews is there a chance you'll end up naked at the end of it.” -Jerry Seinfeld

I hate the term "dating." For me, it conjures up these antiquated scenarios of two people out, forcing small talk on each other until it's time to end the night. Every now and then I'll be out with a group of friends and I get the privilege of eaves-dropping on a couple nearby. They nervously slam their drinks as they struggle to find new topics of discussion to keep the conversation flowing.

Date Idea, Dinner and Drinks

Him: "So do your parents live in the area?"
Her: "I actually never met my mom, but my dad lives in California."
Him: "Oh... okay. Your dad lives locally?"
Her: "Kind of. He's up for parole in 2014."
Him: *drinks*

As I've said, my ideal date is a terrible one, admittedly. I choose my favorite bar, show up early to get a good stool so that I'm positioned nicely with the TV forty-five degrees to my left and my damsel for the night directly to my right. If the conversation wanes, I'm a simple rotation away from watching Blake Griffin crotch-grind a defender's face.

That being said, here are a few dating ideas that he'll actually like as well as some to avoid.

Date Idea, Comedy Club

Comedy Shows
Since it's the guy's job to keep the plates spinning at all times and make you laugh, comedy shows are an excellent escape. This essentially allows us to put the plane on auto-pilot for a little bit and pay some other guy to make you laugh for an hour or two. It really is a win-win. If the guy is funny, we got our money's worth. If he sucks, we look that much funnier.

Getting Together With Your Friends
I know there's this mythical "give and take/compromise" thing that supposedly has to happen for relationships to work, but why steer things into disaster if you can avoid it? Chances are very good we don't like your friends. It has nothing to do with them as people; it's the fact that they're an extension of your life that was there before us. Every time I've gone out with a girl and she decided it'd be okay if she had her friends join, I felt like I was on trial for the entire evening. My favorite was when a girl decided we should meet up with her church group. When I offered some of my red wine to Pastor Tim as "Jesus' blood," I knew the two of us were never going to see each other again.

This actually is a great activity to get involved in with your significant other. You'll both look and feel better. Unless you're dating a workout freak, chances are you wish he'd go to the gym a little more and replace the six pack next to the sofa with one on his tummy. So in five years when his metabolism has been ambushed by Miller Lite and Double Doubles, he'll still look...decent. Which will make you want to find another guy a little bit less. Thus keeping your relationship intact. All because you went for a run. You're welcome.

Date Idea, Picnic

Here's a great idea! Let's pack a bunch of food that isn't going to fill me up, some weak alcohol that isn't going to catch me a buzz, put it into a bag, and let it sit long enough for the condiments to start to go bad. Then we'll bring it to the park, sit crossed-legged on a blanket, and eat! Afterwards we can roll around like a couple of high school students and kiss. But since we're in public, there isn't much of a chance for the sexual activity to escalate! Doesn't that sound like fun?

Even people who don't like sports enjoy tailgating. I know, on the surface all it is is people drinking a bunch of ghetto-swill beer in a parking lot wrought with barbecue smoke and face paint. Of course it sounds stupid, but I have yet to meet anybody, guy or girl, who doesn't enjoy that. And if you're a fan of either team, it's a bonus. Unless you're at The Coliseum and you're anything but a Raiders fan. Then you might end up getting shot.

Those Events Where You Get Dressed Up and Have Your Picture Taken On A Red Carpet
I've done tons of research on this (four Google searches), but still can't figure this out. After every weekend on Facebook I keep seeing couples dressed to the nines getting their pictures taken on a red carpet in front of some backdrop replete with corporate sponsorships. It looks like they're celebrities about to get bombarded by the paparazzi, when in reality I know it's Bill from the gym and his girlfriend who doesn't like me. Isn't Halloween enough of a day to dress up and pretend to be somebody else?

Date Idea, Weddings

I know it's not really a "date," but weddings are fun as hell. If you've invited him in the first place, that means you're probably at a point in the relationship where - with good reason - you felt comfortable enough asking him. Although they're getting excessive these days (would you people please knock it off - you're making me look bad), they're still fun. Even if we don't like to dance, there's still almost always an open bar and an uncle who never lived up to his full potential who wants to live vicariously through us.

Unless things are in excellent shape between the two of you, you're asking for a disaster. You two are on the rocks over something, and you're bringing him into an event where there are usually a dozen hot, single women desperately seeking validation because their friend just got married. Love is in the air, and it might be in the coat room too after he's had a few too many whiskey sours and divulged to "Megan" how he's unhappy because you never like to do anything but missionary.


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Drew is a single guy living in Los Angeles. When he's not bar-hopping with a friend's golden retriever to convince women he has a soft side, he's taking them on short-lived dates. His fickle dating habits and "perspective" almost guarantee he'll die alone. All opinions are his own. Got a question for Drew? Ask away:

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