9 Rules of Dating for Clueless Men

It occurred to me after returning to the dating circuit about eight months following my separation from my ex-husband that dating in one’s 30’s is a good deal different from dating in one’s 20’s. However, some things never change. Men remain, to a large degree, clueless about how to genuinely impress a female…or, at the very least, get her to want to ever go out with them again after date number one.

So I decided it was time to give the guys a “fly on the wall” view of the unspoken rules women carry around in their heads on those first few dates. Please note, however, these rules apply only to high quality females (i.e. not the type who smokes three packs a day and sports a tattoo across her chest that reads “Only God Can Judge Me”).

1) Pay for dinner. It befuddles me that I even have to note this rule, but you’d be surprised how many guys don’t get it. I don’t care if you’re dating an executive powerhouse of a female, pay for dinner on the first date. Now, in the interest of politeness, she might offer to half the bill, but trust me, 99 percent of women expect you to decline the offer and pay for that first date meal. If you don’t, you will look like a clueless schmuck, and, I assure you, she will never return your phone calls or texts. (If you want to make the argument, as I’ve heard some guys do, that you can’t afford to pay for the meals of the 20 women you’re taking out a week, then be more selective, or be a jerk, and don’t pay for the meals of the women you never want to see again—but before you do that, make sure you don’t want to date any of her friends or acquaintances ever. She will tell everyone she knows how clueless you are.)

2) Open doors. Another “I can’t believe I have to tell you this” rule, but there are men who fail on this one, too. Opening the door for women and elderly folks is just plain courteous, and it shows you have at least some breeding.

3) Please wear a clean shirt. You will be judged by how you look, and I don’t mean you have to be drop-dead gorgeous to get a gal’s attention. But make it look as if you put some effort into getting ready for this gig. The three-piece suit isn’t required, but crisp, clean clothes and well-groomed hair and nails are. Show up with that lunch spaghetti stain on your shirt, and you’ll be lucky if you make it out the front door with her…if you do, she is incredibly generous and polite. Nothing says “I’m a sloth and I don’t care about you” more than rumpled, stained, or uber casual attire.

4) Talk about something or someone besides yourself. There is no bigger turn-off than a guy who can’t shut up about how awesome he is or who dominates the conversation. No. 1—it communicates you’re insecure. Confident people don’t feel the need to talk incessantly about themselves and their accomplishments. No. 2—you will bore her to tears. You may find your job enormously interesting, but chances are, she doesn’t. Plus, who the hell wants to talk about work on a date? Not me. I get enough of that in my own office….

5) Don’t ask if you can do your laundry at her house. This is not college, guys. Fix your washing machine, or buy a new one. And if this is some lame excuse to stay over, trust me, you can come up with something better.

6) If you’re interested, let her know. Suck up some courage, and ask if you can call her or go out again. I know your ego is fragile, but if she turns you down, what exactly do you have to lose? That’s right. Nothing. So take a risk, and let her know you’d like to see her again. There are a few women who will pursue you, but most figure any guy worth having is one brave enough to walk a little ways out on a limb for them.

7) Please learn how to kiss. It is beyond shocking how many men do not know how even after a decade and a half of marriage and five years of dating. Trust me, bad kissing is a deal breaker. Call us ladies shallow, but it’s true. No one feels like being deep throated by your megaloglossia on a first date. Chill on the probing tongue action, and learn to kiss like Romeo. You can salvage a lackluster date with an incredible kiss for reasons I probably don’t need to go into….

8) Do not make a move for sex on the first date, the second date, or the third…. Unless you are going out with the aforementioned lady with the tattoo across her breastbone. No. 1—it makes you look like a prick who is only interested in one thing. And while that may be the case, be aware that it’s not likely to win you any bonus points with your date who much prefers the idea that you are charmed by her sparkling personality. No. 2—first time coitus is almost always mediocre at best. Let’s face it—she’s a new partner, and you have no idea what drives her wild. Do you really want her first impression to be that you are, at best, a mediocre lover? She will forgive mediocrity later if she’s in love with your character. And she might even teach you a thing or two….
9) Before you ask that attractive, smart, and successful woman out, make sure you like arm candy with a brain. Sadly, far too many men, even incredibly intelligent and powerful ones, have trouble with women who can hold their own in talking stocks at a cocktail party even while being the hottest number in the room. If you can’t get over yourself and realize you must be pretty awesome to attract such a female, don’t even bother wasting her time. On the other hand, you might keep in mind that every guy in the room is not only going to be jealous but perhaps even wondering how you landed such a prize. Of course, I don’t have to tell you what conclusion they’ll draw about you….and your…ahem, abilities.