Guide to Post-College Dating

Background

The other night, I had dinner w/ my friend Samantha (a really pretty girl I grew up with in the Jersey Suburbs). Having spent the past 11 years of my life in Manhattan, I hadn’t seen her since we graduated high school.

While catching up, she was explaining to me some of the really bad dates she’s been on recently. As a serial dater, after hearing her go through these horror stories, I feel compelled to impart some advice for some of you guys out there. [Pause for Reader to roll their eyes]. Hopefully you’re already employing a lot of these things and I’m just preaching to the choir, but if not, might wanna pay attention.

Since a lot of NYC social life revolves around eating, I’ll discuss some things to think about during a proper dinner date.

1. No New Places

Take her somewhere you’ve already been before and know is good. It should/can be new for her, but you want home court advantage where possible. Friends’ recommendations may seem like safe bets but are riskier than you think. Good rule of thumb, don’t bring her to any place that has a TV.

And the VE and E restaurants in Zagat don’t
work with girls who have dated frequently and are evaluating you on your restaurant choice. Be
careful that you don’t come across like you’re trying too hard. If she’s got overbearing parents, talks with a nasal voice, and has a penchant for complaining however…

2. Be Early

Most restaurants that you’d bring a date to should have a full bar upfront. Instead of having her get there before you and looking like a hooker at a hotel bar, arrive 15 minutes early and get a drink.

Chat up with the bartenders and consult their views of the wines offered at the restaurant. You’ll look a lot better later when your server asks you about wines and you have your answer ready without frantically scanning the right side of the list like a moron.

3. Give Her The View

When you’re being seated, the simple rule is that the girl gets the better seat. How do you define the better seat? The one that offers the better view of the restaurant (ie, NOT facing the wall or the bathroom doors).

And pull the table out so she can slide onto the couch while you take the chair. This is especially important because no girl wants to feel her muffin top rub up against the table.

4. Be a Thought Leader

Have a few items on the menu in mind that you can recommend. Many girls tend to be cautious when ordering (fear of looking like a pig, worried about ordering something too expensive, etc), so alleviate their anxiety by saying, “I think you’d really like the [item] here.  They’re known for it.”

Besides, inability to make an executive decision isn’t exactly a turn on. Again, you can consult the bartenders in advance if you get there early.

5. Order Dessert

It’s pretty simple. Girls all want dessert but the Anorexic Club pretty much forbids them ordering it. Just say something like “Well, we’re definitely splitting something so how about this [chocolate thing]?”

Then quickly follow up with, “Yeah, don’t worry, we can just have a taste. No need to finish it” all the while knowing she’ll shovel down that entire chocolate lava cake before you get 2 bites in.

6. Screw The Dutch

If the dinner’s going well, you should man up and take care of the bill. Typical protocol is the girl excuses herself after the meal before dessert arrives. While she’s away, flag down your server and slip him your credit card. If she’s holding it in, you can excuse yourself and track down the waiter while she checks her cell phone for text messages about you. Then when the bill arrives, all you have to do is sign after adding a generous tip (if that extra $5-7 is going to break you, you shouldn’t be eating out).

However, if she’s given suggestions that she may be a gold digging whore, skip that step and just wait for the bill to come and see if she does the infamous “fake purse grab” as if she genuinely intended to pay her portion. You should pay the bill anyway (after all, you are a man) but just observe how they react here. I know you girls don’t pay for dinner, but at least do us the courtesy of pretending like you were going to. And ladies, pause just a LITTLE bit in between “Are you sure?” and “OK, thanks.”

7. Have An After Dinner Plan

Some restaurants are really great venues but have horrible locations for after-dinner drinks (which if she’s not a clueless moron, she should at least offer to pay for since you picked up dinner).

If you planned well, there should be bunch of different bars close to the restaurant. This will help with Borderline Dates who aren’t yet sure if they like you or not. Otherwise, with a requisite cab ride, you run the risk of hearing the dreaded “It will be 2 stops.”

Bad Date Ideas that Sound Good At First

1.  Movies. This is something you did when you were in Junior High because you didn’t have an apartment to hook up at, so you used the AMC or Loews as your venue of choice for pecking and heavy petting. Why aren’t theyg ood now? You don’t really get to talk, or ever get to look at her chest when she’s texting on her cell phone about how you didn’t take her to dinner. Besides, where do you find a good lap blanket these days anyway?

2. Bowling. It may seem like a very good way to show her you’re down with how the middle class lives (Hillary, you should have taken note of this), but when you’re only 2 at a lane, either you’re bowling or she is. You do the math.

3. Your Friend’s Birthday Parties. Yeah, great… you know everyone there so you look like a popular guy. She, on the other hand, probably feels out of place. This is a high risk move, gentlemen, especially if she’s not that outgoing. And if she IS extroverted, your drunk guy friends (like me) may end up hitting on her and giving you unintentional competition for her attention. Proceed with caution.

4. Clubs. OK, you may have impressed her by getting into the hot spot with the velvet rope and the overdressed giant guarding the door, but now you’re INSIDE.  If your date’s hot, then you’ll have all the slick haired guys hitting on her every time you turn around to order her watered down $12 vodka cranberry and if they’re NOT hitting on her, you’ll be wondering to yourself, “What’s wrong with this girl?”