Dating for the Clueless - Part 2

Let's recap: you called the woman, you asked her lighthearted questions about ice cream and favorite beaches, you artfully avoided mentioning shadow puppetry and her bust size (and what you'd like to do with said bust) and you scored some face time (which you asked for over the phone, not via text or email).

Now what?

While there's no doubt that you will win her over with your charm and good-looks, there are a few things you need to do before you get there.

1. Plan something. You'll have gleaned from your light, yet curious banter what she does and does not like. Creativity gets you a lot of points, but don't be so creative that there is no environment to further get to know one another. (Creativity also helps if you are financially challenged.) Dinner at a fantastic restaurant is fine, but a picnic dinner could be even better...unless it's on a grassy knoll and she's allergic to grass. Also, if you plan the date, you can control how much money you spend. Groupon, Living Social, Trubates...these are all your friends.

2. Make an effort on your appearance. I'm not saying you need to consult with GQ first or even put on your church shoes, I'm just asking you to think about the impression you're trying to make. Baggy sweatpants, an old, ratty t-shirt and dirty tennis shoes are not the way to go...unless you're doing something that requires those kind of clothes. (And if you are, make sure your date knows this!)

3. Most importantly, make sure you're clean! Unless you've met a woman who loves a funky man (and has told you as much), please bathe...just not in your cologne. And don't forget to brush!

Once you're there...

4. As you're getting to know her, again, keep it light and appropriate. Dates can easily morph into interviews. What do you do for a living? Where did you go to school? How long have you lived in the Bay Area? Have you ever been married? Snooze. Yes, this is all vital information, but spread it out. Ask some interesting questions. What's the best cocktail you've ever had? Favorite vacation spot? How do you feel about marijuana? Have you ever danced with the devil in the pale moon light?

5. Be confident! If at some point, you realize that this awesome woman is waaaaay out of your league, don't tell her that! She A. probably already knows and/or B. sees something in you that she likes. Most women respond favorably to a man who appears and behaves as if he's comfortable in his own skin. As we get to know each other better, there will be a time and place for all the baggage and vulnerabilities to be exposed. That is NOT on the first date.

6. To quote Chris Rock: "There are only three things women need in life: food, water, and compliments." Complimenting is a very subtle and delicate art. Too many and you come across as pandering and insincere. Too few and you're a self-absorbed a$$hole who doesn't appreciate how lucky you are to be in her presence. I know, it sucks for you. Here's a little help:


Yes: I didn't notice how blue your eyes are. They're really pretty.
Uh-uh: You're so beautiful, girl, I just feel so lucky to be with you, I can't believe you chose me.


Yes: I like your earrings/dress/hair cut.
Uh-uh: Can I marry you, because you are obviously the most wonderfullest woman I have ever met.


Yes: You have a beautiful smile.
Uh-uh: It's not your beauty, it's your booty. You got ass for days!



7. Now this may be controversial, but it's your treat. Double standard, whine, whine, whine, equality, blah, blah, blah. At the end of the day, men make more money than women doing the same job. The end. (P.S. Don't be a stingy tipper. Not a good look. Unless the service was incredibly bad, 15-20% is the standard.)


8. If the date is going well, she will subtly let you know. She'll touch you on your arm, hand, knee and won't be repulsed when you reach to do the same. Pay attention to the body language. When her arms are crossed and her body is angled away from you, it might not be the best time to try to kiss her. Admittedly, the kiss goodnight is always a little tricky. Although she be attracted to you, she might not kiss on the first date. Some women have arbitrary and silly little rules like that. However, if things are going well, she'll let you know if it's cool for a kiss; hell, she may kiss you! 


9. Last but not least, if you enjoyed yourself and want to see her again, FOLLOW UP. FOLLOW UP, FOLLOW UP, FOLLOW UP. That means calling her...on the phone...and conversing with her. Sending a little text, making sure she got home safely is also a really good and chivalrous move. Bonus points.


Rinse and repeat.


Sidebar: 
Now if this is someone you've met online or is a blind set-up, I highly recommend going on an abbrevadate (thanks, AS). The abbrevadate is a time-limited activity (lunch, brunch, drinks) that should happen in the morning or early afternoon, so that if you can't stand each other, there's an obvious out. "I have to run, I have to give my cat a flea dip,"* is a totally feasible reason for your activity to end by noon on a Saturday. One of the best activities for an abbrevadate is meeting up for coffee, even if you don't really drink it. It's cost-effective and espresso-mocha-choco-lattes (no whip cream, watching the waistline) are the perfect excuse to start your day with a liquid dessert. The benefit of an abbrevadate is that if you're not clicking, it's over quickly, you've spent maybe $20 and you can go about your day. However, if you're really digging each other, the abbrevadate can easily transition into a date-date. If you follow the suggestions above, you may just increase the likelihood of spending more time with her.

I'm not guaranteeing that these ideas will get you another date; there still has to be chemistry between the two of you. However, even if it goes nowhere, it is highly likely your date will walk away feeling good about you...and you never know, she might have a friend that's a better match. Plus, you'll know that you didn't fall into the "Girl, no he didn't" file and are being discussed over margaritas and guacamole.




*Some may argue that being truthful and acknowledging that you're not having a good time is the more mature route, but c'mon - few people are that honest (or mature).