The High Status Male

Mike, I have trouble with the “clever wit” aspect of the flirting game.  I freeze up and can’t think of anything funny to say, and it feels like I should be doing something to lighten up the mood.  It’s really hindering me.  Any suggestions to get me started?

Also, what are good things to talk about in a first encounter to get things going on a romantic track right away?  I always feel like a goddamn interrogator and it doesn’t work, but I don’t know of any other way to keep the conversation flowing.

Jack

Hey Jack,

Clever wit only means that you make funny observations about certain things going on around you, or about universally understood people and events that are currently cooking in our popular culture.  (If the premise of the joke is not universally understood it qualifies as an inside joke.  Not good usually.)

Remember how Jerry Seinfeld used to do it?  Find his re-runs on cable and study them with a more trained eye if you never watched him before.  His is the perfect kind of clever but mostly non-offensive humor that women really dig.

Don’t go overboard with the jokes though, or everything about you will seem forced and unfunny.  And don’t forget that timing is everything in humor — make sure that you pick your spots carefully and only roll out a clever remark when the moment seems just right.  It’s your keen recognition of that certain moment that I think defines what is commonly understood as a “sense” of humor.  In other words, avoid any attempt to force the gag if there isn’t something juicy to grasp onto.  Better you say nothing than take a shitty stab at humor.  (Be careful not to make any jokes about HER or say anything that could be misconstrued as a put down, of course. I shouldn’t even have to say this.)

It’s tough to coach humor — it takes a bit of observational sensitivity mixed with an ability to quickly find the ridiculous side of things, and then point them out in a “cute” way (delivery).  That delivery can vary from deadpan (straight faced) to a wild man persona like Robin Williams, though I would recommend something in between.  This is drawn from your personal style.  Observe, comment, get a laugh.  Then let it rest for a while.  Humor is like salt & pepper — just a touch here and there.

Don’t come off as being too well-rehearsed like you’re doing a goddamn comedy routine!

Instead of dry questioning, talk about the interesting things happening in YOUR life, but in a way that draws her out and gets her talking about her own interests. “I was at the gym working out the other day and blah, blah, blah… tell me, what sort of things do you do to keep yourself in such great shape?” Like that.  This tells her something interesting about yourself, gets her to talk about herself in a way that might uncover some common ground between the two of you (you’re fishing around for topics), and sneaks in a sly compliment about her great looks as a bonus (that’s always the best way to lay in a compliment… with subtlety!).

Always try to stay laid back — ceaseless interrogating makes you seem intense and inexperienced, and ratchets up the pressure on her too, because it becomes obvious that you’re trying to “pick her up”.  The discomfort this creates will make her want to get away from you ASAP.  Lighten up, loosen up… and act like you do this stuff all the time (even if you don’t, how the hell can she possibly know that?…)