Valentine's Day Dates: Do's and Don'ts


Here’s some unsolicited dating advice from two commitment-phobes who think V-Day is a vodka thing.

The Location

Rachel: If you want to do something super romantic, I’d suggest going for a sunset hike or offer to cook dinner at your house. I would never actually do either of those things, but I know people who have and they aren’t single anymore so it obviously works. However, if this is a first date you probably don’t want to put yourself in either of those hyper-intimate situations because they could lead to full murder, so maybe just opt for a cozy, locally-owned spot on the grid. Want fancy? Grange or Mulvaney’s. Want a lil’ cheese, wine, and intimacy? Cabana or The Rind. Want a bomb three course meal at an Irish pub? de Vere’s. Want beer and a soft pretzel the size of your face? Firestone.

Patrick: Location is everything – and so is decisiveness. If you’re asking someone on the date, think of two locations of varying type (Italian vs Mexican, crowded vs intimate) and suggest them both to your paramour. They’ll appreciate the choice but also that you took the initiative in following through with concrete suggestions after asking them out.

The Conversation

Rachel: If you’re like me and tend to overshare about the life you lead and the one you eventually want, then it’s best to come prepared with specific talking points and questions to keep you on track. Don’t just ask the typical questions like “what do you do?” Girl, you know what he does from your earlier Google search so ask something cooler like how long it takes him to grow a full beard. He’ll be totally weirded out but hey, points on originality. Be polite and look him in the eye. But don’t like, creepily stare. Put your phone away, but definitely check it when he goes to the bathroom. Laugh at his/her jokes, but not if they aren’t funny. Kidding. Definitely fake laugh. But don’t fake laugh like me where I half-smile and an animal-like grunt comes out of my mouth and my eyes are rolled in the back of my head as I reach for my drink. Because that’s rude.

Patrick: A good rule of thumb is to always have three funny stories about amazing things you’ve done in your life and be prepared to tell at least two. If you don’t have three amazing stories of things then why are you trying to settle down – you haven’t lived!

All in all though, your parents were right – Honesty is the best policy. When on any date, be it the first or the fifth, hold tight to this old adage and try not to embellish or lie. Your partner wants to get to know the “real” you – so be an open book and allow for questions. Just maybe leave out the part about being a registered sex offender.

Also, never order a salad. No one has ever looked good eating a salad while having story time.

The Check

Rachel: If you’re just starting out together, I think the person who suggested the date should pay. If you go to a second location that night, then the person who didn’t pay the first time should absolutely…offer. And even though I think it’s proper for the asker-outer (?) to pay, I always reach my hand into my purse and pretend to feel around for a wallet because that’s the American thing to do. With that said, I certainly don’t get offended if on the first date he says, “so, you wanna split it?” C’mon, it’s 2015! In fact, if he asks you to split it just tell him to put his card away and pay for the whole thing! Then ask the server for a to-go bag for his balls.

Patrick:  I’m a big believer in going dutch if the first date is an online meet up. Too often, people abuse online dating for free meals and ain’t nobody got time for that.

For special occasions I am a big fan of playing the gentleman card and going all out. Everyone needs a good pampering now and then – and in those situations I’m all about racking up airline miles.

Overall though, it comes back to equal expectations. I think in any relationship alternating dinner payment is the right thing to do. The moment you expect someone to pay is the moment you’ve become dependent in the relationship. And nobody is interested in dating a beta.

Hooking Up

Rachel: I think I read somewhere that sex is really special for some people and they prefer to wait until they’re “ready.” For some that means waiting for the moment your partner does something really nice or maybe it’s just that fifth glass of wine. Others say that the 3.53 date is the “right” time to have sex. Um, what is a .53? Anywho, deciding when to have sex with someone isn’t a scientific algorithm and it differs from person to person. My advice: If you like the person and you think having sex with them would be fun then you should have sex with them and have fun.  If you’re having doubts like you don’t think you’re ready, you’re afraid if you “give it up to early” they will “think less of you” or blah blah blah, then don’t? I think.

Patrick: Yes. Always. Be safe, have fun, but remember these two steadfast rules on any date:

1. Limit Your Alcohol Intake. Alcohol is to you like Ben Affleck is to any movie: in small amounts, it can be enjoyable, but as soon as it takes over, everything turns to shit real fast. Your date will start saying things like “This has gotten embarrassing. We should just go.” When you’re that drunk, or what I like to call “Reindeer Games drunk,” you cease to be cool and begin to sabotage the shit out of yourself.

2. Never Agree to Posing Naked. I understand the kinky turn on nude photos can provide. Just realize that agreeing to a full frontal photo shoot means that in the not-to-distant-future some asshole is going to post YOUR asshole on their RedTube channel.

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