Anytime I hear “Hey Ya” on the radio — sometimes even on a date if it’s played in a bar — I can’t help but snap back to the night this laaaaaaaaaaaaaaaaaaaadddddy gave me a little case of something-something. Nothing major — in fact, it’s so minor I hadn’t even heard of it. And kids give it to each other with wet towels or something. It went away and will never come back.

What happened was I was on a 2nd date with my second tall woman (5’9) at her house in Nov of 2003 — Nov. 1st to be exact. We made out for hours and watched SNL (OutKast was the musical guest) and when it got to be around 2am, I asked if I could sleep on the sofa not wanting to be on the road that late. She kept saying, “If you stay here we are going to sleep together.” I kept saying, “No, I just don’t want to have an accident driving home (she was about 25 miles away) and I will be here on the couch.”

After a bunch of back of forth in this arena, we start making out again and then at some point, she goes, “Let’s have sex.”

Oh! Okay…we have sex — with a CONDOM — she doesn’t seem to be enjoying it and I don’t get off.

In the morning, I’m thinking I’m going to get off, but no, she rushes me out of her house.

Then I get an e-mail saying she had fun, but doesn’t want to have sex or see me again.

About a week later, I notice a little something-something (not crabs or a rash, btw) and go to the doctor. He’s like “You got an STD.”

I freaked. ‘What — I’m so low risk! I wore a condom.”

“It was in her crotch.”

Damn that 70′s bush she was rockin’!!!!

Then I find out the medication isn’t covered by my insurance — so that turned into a $325 date.

And the doctor encourages me to let her know.

I didn’t want to call or send an e-mail.

So I wrote something on a 3 x 5 card (“Hey, hi, remember me…listen, I just went to the …. “) and put it an envelope and mailed.

Exactly 1.5 days later (probably as soon as she walked through the door at 5:32pm), she calls.

I let the machine get it. And I erase it w/o even listening to the message.

My 2nd date philosophy is a simple one: If they were attractive enough, nice enough, interesting enough (or interested in me), I’d ask them on a 2nd date. Maybe I wasn’t / I’m in LOVE, but thought/think that’s there’s a little something there, I initiate another get-together.

I like to give women a chance I think a lot of women don’t give me.

If I was bored or sensed they were bored or not interested or they weren’t cute enough, I wouldn’t / I don’t.

I have a feeling that women (ok, a generalization) don’t operate like this — if they didn’t feel butterflies or didn’t see you as their future husband during the coffee date or don’t see you ravaging them in bed, they don’t bother. Too many buses coming down the pike to bother with any one particular bus.

I did have a date about 2.5 years ago that went so well, I actually walked away thinking “hey, I think that girl will be my next girlfriend” and was absolutely dumbfounded when she didn’t go out with me again (she pulled the “2nd date shuffle” on me). About a year ago and wrote her and kindly asked her if she remembered me and that I was having a hard time getting 2nd dates if there was something I did that turned her off.

Her reply:

Honestly, I don’t remember that well.  I know you didn’t say or do anything wrong – I would remember that.  I think I was exhausted by dating at that point and a little bit burned out on the process.  I was going on about three first dates a week and expecting some miracle or lightning bolt to happen on one of them.  I rarely went on any 2nd dates – because I didn’t hear back from people or I was too tired to respond to someone – and eventually just cancelled my membership out of exhaustion.

Three dates a week? That’s even too much for me and I date pretty frequently.

Another weird story.

I went to a speed dating event in fall of 2008 — a “Cougar” speed dating event — it turned out to be a lot of Plain Janes and heavyset and black and Asian women in their 30′s and 40′s and very few men.

The first woman I was matched with was an angular, slightly uptight woman in her mid- 40′s. Think Meryl Streep’s odd sister. Hair up or pulled back (not a good look for a dating event). Her name was the name of a very popular nonsensical children’s song in the 60′s — like “Mahna Mahna Ma.” Apparently her older sister couldn’t stop singing the song and kept pointing to her — as a newborn — and her parents just named her “Mahna.” It was the Sixties and it sounded vaguely exotic so they went for it.

I happened to know the daughter of the guy who wrote the song she was named after and mentioned it straight away which got her attention.

She was an odd bird, this woman — an artist who made weird things out of balsa wood and painted them. Recently divorced, she was living with her sister and their kids. There was something vaguely attractive about her even though her features were bird-like — she was pretty witty which was a nice change.

Then our 3 or 4 minutes were up and the speed dating went on. When it was over, we ended up walking out together and she was 5’10 (something you don’t notice at speed dating where all the women remain seated.). I walked her to her car. She awkwardly gave me her number.

We made a date. She meets me for coffee across the street and wow — she looked amazing — her hair was down, she was wearing a tight white stretchy shirt and was unusually busty — something I hadn’t noticed before. She was still a little weird — I couldn’t put my finger on it — definately some depression in her history (I think we both might have bonded over that)…

I thought about it for a day and then sent her an e-mail. I was attracted to her, but she seemed weird and our rhythms seemed off. But I wanted to fool around with her. So, I tried something that strangely worked before — I sent her e-mail that said I was attracted to her, but felt we weren’t boyfriend/girlfriend material, but still strongly drawn to her and didn’t know where she was in her life and didn’t mean to offend her, but if she wanted to “explore” that purely physical attraction, I was game.

She e-mailed me back — she was in!

We made a date for her to come over my apartment. Here’s where it all went wrong.

She shows up, hair pulled back or up, wearing a smells-slightly-musty old lady sweater. As soon as she came in I felt there was something wrong. She sits on the couch, I ask her if she wants some wine? She says yes, I go into the fridge a take out a bottle of white.

I hold it out to her and ask if white is OK.

Her response: “Is that the wine you use to get women drunk with?”

You know those stories where a guy is on a date with a woman and she’s willing / about to sleep with him and then he says something so incredibly stupid, her libido takes a nose drive and she is done, done, done. All her good feelings and desire for sex just gets wiped clean like a shaken Etch-A-Sketch? Well, that’s exactly how I felt. It just flew out of me. I totally got that.

“Um, no….it’s the wine I cook with.”

We sit on the sofa and she moves to the OPPOSITE END of my 8 foot couch and we watch the documentary “King of Kong.” She’s being really prickly, she’s like a few feet away from me, I don’t know what’s going on, so I figure I’ll let her drink her wine to come off the ceiling.

About 20 minutes in, she pops: “Hey! I don’t get what’s going on here — you invited me over to fool around and we are just watching this movie!”

Kinda expecting this, I said very calmly: “Look, I don’t know what’s going on either — you’re sitting on the other end of the couch, you made that crack about me getting women drunk — you don’t seem like you want to be here at all.”

She acknowledged this — said she was nervous, said she wanted to be there.

I said, okay, well, let’s kiss and see what happens.

We are standing up at this point and I kiss her — and NOTHING. Absolutely nothing. Plus I got a wiff of that sweater.

“I’m sorry, I’m not feeling it” I said or something like that and she literally fled my apartment. Like within seconds of me saying that.

I’m not proud of all this, but I think this woman, conciously or unconciously sabotaged our make out session. The hair, the sweater, the wine crack, the couch distance. I mean, if you were going over someone’s home to specifically sexually “explore” with them, wouldn’t you dress a little sexy? Act a little sexy?

Luckily, I don’t hear that 60′s kid song much.

On a whim, I bought a single ticket to see Tim Gunn lecture at USC last night (10/29/11). Tim was the Dean of Admissions when I was a student at Parsons and for some reason, he knew who I was. It’s been weird seeing him on billboards and the sides of buildings and on the Oprah Show (“Wasn’t I supposed to get famous? How did an administrator from my college get super famous?”)….

It’s funny, I was speaking to one of my best friends and she said, “Wow, that would have been an awesome thing to take a girlfriend or a date too.” Yes, it would have been, but at present I am in the ‘wrangling-first-dates’ stage of dating..but maybe that’s good place to meet young, single women — I might be the one of the few straight guys there.

Once I was inside the hall and directed to the general admission balcony upstairs, I realize, I’m sitting 2 rows behind a woman I kind of had a bad date with! At the rate I date and doing the things I like to do, it is inevitable I am going to run into someone I went out with and made a vague promise to about getting together again at the end of our uninspired or pained evening.

This woman was a woman I met on match, maybe in the spring — a woman who I actually agreed to be just ‘buddies’ with because she wanted a child (RIGHT NOW) but we had similar interests. So we met at a storytelling event.

Now when she called me to say she’s walking toward the line outside the storytelling event, I looked up to see this brunette in her late 20′s and a little beige blazer, tight jeans, her oversized bust bouncing as she’s strutting down the street, carrying a — wait for it — a BOOK. (The story about that girl will be be a whole other post), but then my brain realizes that can’t be the woman – she should be talking on the phone — to me — right now.

Then right behind her, is my “date” (well, “buddy date”), let’s call her ‘NoCal Hippie’. NoCal Hippie was really out of touch with the SoCal look (i.e. not looking like a middle-aged hippie) — Birkenstocks, frizzy, unkempt, salt and pepper hair in BRAIDS (????), that face peach fuzz so thick it looks like long blond jaw line sideburns, a men’s plaid shirt, no makeup, mid 40′s — she looked very ‘Pacific Northwest Organic-Might-Be-Gay.’ I had feeling her few Match pictures were misleading! At a distance or weird or flattering angles, I had ‘filled in’ the gasps and made her prettier than she was in my mind. So luckily this wasn’t a date!

But I couldn’t really get over the bait-and-switch and this OTHER hot girl — “Book Girl” was in line a few people behind me and it would have been easy to follow her in line and stand right behind her and chat her up, but I had this buddy date with NoCal Hippie.

Then NoCal Hippie gets an ORGANIC HOT DOG from the hot dog stand next to the line (which was the only food around — the place didn’t serve food), a big fat smelly, organic hot dog with sauerkraut and onions…

…and eats while we wait to enter and then I have to smell her organic hot dog breath for the rest of the night. And then when it was over I booked (I did manage to hit on ‘Book Girl’ during the evening without getting caught, but again, another story for another time) so fast. And never called or e-mailed her again.

And then I see her last night. Two rows in front of me.

I moved to the other side of the theater and sat close to the exit for a quick getaway, but when it ended, they were only having people exit from the exit on the other side, closer to where she was. Luckily, she left before me and I did not see her at all.

In acting class I learned about the “moment before” — before you enter a scene, your character has had a previous moment, a life before that scene, which directly effects how your character is going to act in the present moment. Was he just yelled at by his boss? Did he just get smiled at by a pretty girl? (Often when you only get “sides” in an audition — just the few lines you are playing — you have to make up a previous moment for the character.)

I mention this because I think the “moment before” a date is pretty critical, especially with women, who are unusually sensitive to moods and their surroundings. That’s why I don’t like to meet women immediately after they’ve worked late at the law office and still are in their pants suit and in ‘attorney head.’ There is something to be said about the days (30′s? 40′s? 50′s? 1880′s?) when women spent a few hours “preparing” for a date, bathing, relaxing, grooming and transitioned into “date mode” and stepping into their femininity.

What happened to me last week was when I got to the vegan hipster bistro to meet my date Francesca, she was in the midst of being hustled.

I got there 6 or 7 minutes late (I called ahead while in terrible traffic) and I saw what looked like her at a table outside and she was sitting with another woman. There were drinks on the table, so I thought maybe that’s not her — these ladies have been here awhile. So I call and then hear HER phone ring at that table. She says to woman she’s sitting with (her back facing me), “You gotta go,” with an unusual amount of anxiety in her voice.

I approach, stand in front of the table and they are arguing.

Woman (mid 40′s, black, dreds): “I told you how much before I sat down.”

My Date: “No, you said it was free.”

Woman: “No, I did not.”

(Now, I don’t understand what is happening — I thought maybe she had a business meeting before me — she was a freelancer –and my head isn’t really clear since I just spent an hour in traffic trying to get to Hollywood in what would have normally taken 35 min – 45 minutes max)

Then, flustered, my date says, “Okay, fine — I’ll pay you, it doesn’t matter,” reaches in her purse, thrusts the Hustler a $20 and the Hustler hustles out of there so fast, there was practically a puff of smoke where she had been standing.

Then my date tells me what happened — the woman approached and offered a FREE palm reading.

Now, I’m from back East (lived in NYC, went to high school in the inner city) — nothing’s EVER free — there’s always a catch. When people try and hustle me here in L.A. I say, “Dude, I’m from NYC — we INVENTED this.” One guy actually said, “Sorry, man” like he was violating my patent.

So this lady’s hustle is she says it’s free, but then says she didn’t say that, then out of social awkwardness and social anxiety and white guilt, the mark gives up the money that never would have if they knew it was $20 at the start.

So, understandably, my date — who is BREATHTAKING — pretty in her pictures, but just stunning in real life — is a little shaken.

I tell her a story how I got hustled in L.A. in a faux almost car accident to make her feel better. She comes off the ceiling a bit.

After an hour of nice chatting and laughs, she announces, “Look, I’m just getting a friend vibe from you — I just wanted to be honest, because your profile says you appreciate that, I mean, I’d go out with you again to get to know you better, but romantically I’m kinda on the fence so I’m not making any promises — I just want you to know if we go out again.”

(Now this was a woman who e-mailed ME first a note that said in the subject line “D — You look and sound absolutely fabulous” a couple weeks before)

Me (recovering from the shock, trying to keep a smile on my face): “Wow — that’s the first time in twenty years anyone’s told me that even before that first dated ended. So, just so I’m clear — we can go out again, as friends, but with small portion of romantic potential on the side?”

She laughed and nodded.

I picked up the check and got a “awwwwwwwww”-our-chests-are-not-touching-pat-on-the-back hug.

I bet if I knew what was going on and told the Hustler to get the fuck away before I called the cops, she not only would have not dumped me at minute 55, she probably would have made out with me, having stepped into my masculine and saved her. I bet something inside her was blaming me for being late, ’cause if I was on time, she wouldn’t have gotten hustled. She didn’t feel SAFE on some primitive level.

Had I just gotten there a few moments before…

Sometimes people get sick.

On dates.

It’s unfortunate. But it happens. We’re all human, you know?

And this wasn’t even a date! Full story below:

***

I met Erin at a singles mixer (one of my last) — after having almost every woman there shuned me for being 5’7-5’8-ish and flock to the tallest guys in the room, I happened to start talking to this very thin Jewish girl (my height) from back East. She was smart and clever (Ivy grad apparently) but really wasn’t my type (a little too Jew-y for me — meaning, she looked like she could be my cousin or sister — a little too close to my own DNA).

Erin was mid 30′s, divorced and we had an unusually frank talk about relationships, the sexes, dating and ended up just glued to each other for 90 minutes. I remember she playfully teased me about taking her number down with a pencil: “I don’t remember the last time I saw a pencil — are you taking the SATs later?”

I called a few days later.

Nothing.

About a week after that, I think I sent an e-mail that said something to the effect of ‘It’s ok you don’t want to date me, but I really enjoyed our talks if you wanna be buddies, I’d like that.”

She called and left a very warm, but strange message apologizing for blowing me off and how rude that was, but she had a “very specific reason for not wanting to date…that I probably hadn’t heard before….”

Huh…

I call. She tells me she can’t date me because she has cancer.

After I say I’m sorry and ask “Why were you at a singles party.” She says cause all her friends were going and she was hanging out with them all night, in the same car.

So, she says let’s be buddies. Okay great. A couple weeks later, she invites me to accompany to her the last concert at the Disney Hall that season.

Okay, classical music not really my bag and either is driving to downtown at rush hour on a weekday night from Santa Monica, but she extended an olive branch and wants to hang out and what the hell.

I pick her up at her apartment — about 15 minutes away from me — in the opposite direction of where we need to be. I’m standing in front of her house with no access to a buzzer or a door. I call. It GOES STRAIGHT TO VOICE MAIL. For the next 15 – 20 minutes.

Finally, I think at minute 16 she comes out, saying she LEFT HER PHONE OFF. (This is a big pet peeve of mine — and its happened a few times — meet the woman at her house — when you can’t access the door — and her cell is off even though she’s expecting someone).

Okay, now we are running late, which makes me a little crazy but we make our way downtown (easily an hour ride). She admits she was once the “villian” on a reality TV show from 10 years ago (????)

Finally we get to the Disney Hall (and downtown makes me crazy — it’s a lot of one way streets) and in our seats.

A few months ago, I got a strange e-mail on Match. This is all it said:

You’re cute and fun and I’d like to make out with you, no kidding. Are you up for it? – Patty

You don’t get many of these. And I don’t know what to make of it — does she just send this to a million guys and see who bites?

I look at her 3 pictures — she’s cute and looks a lot like Pam from ‘The Office’ (my celebrity crush), but there’s one picture where she looks older and less attractive than the others.

Then I look closer at the pictures I like — they don’t look like photos of a 45 year old (which she says she is), they are definately the pics of a woman in her 30′s. Early to mid 30′s. Upon closer inspection, like I’m working at a CSI Dating Crime Lab, I can tell they are photos from A FILM CAMERA. Like with grain. And not from a digital camera. So…these pics are AT LEAST ten years old.

Then she starts IM’ing me on Match while I’m analyzing these vintage photos and she keeps complimenting my looks and every time I try and change the subject, she keeps coming back to making it flirty. After a few minutes, she IMs her phone # and asks me to call.

I shouldn’t. I really shouldn’t. But I call.

And her voice is TERRIBLE. Warbly and off-key like the voice of an old lady. Like Mrs. Howell from Gilligan’s Island. But deeper. And drunk. Like a drunk tranny imitating Mrs. Howell at West Hollywood Halloween party.

Very quickly in, she starts talking dirty. And I change the subject.

“So…who do people say you look like?”

“When I was younger, people said I looked like Linda Ronstadt.”

Whaaaaaaaaaat? Red flags are dropping all around me. Linda Ronstadt? A reference from 1983? That’s her celebrity look-a-like? And it’s 27 year old reference?

Then:

Her: “I want to tea bag you.”

Me: What? What’s that again? (I thought only guys did that)

Her: You get your balls lightly sucked. (sluring) Do you like to have your balls lightly sucked?

Me: Um, yeah, I don’t have a reference point for that…actually.”

Her: “I am making you uncomfortable?”

Me: “Look, I’m just a Jewish kid from Philadelphia — no one prepared me for this.”

And I weaseled myself off the phone.

1. If you don’t fake the move to the purse, please at least say ‘thank you’ if he pays for your meal.
2. Dude, just pick up the check – it’s the cost of dating. My new rule? WWGCD – What would George Clooney Do? He’d pick up the check and not even blink.
3. People look like their 2^nd worst picture. Not the best, not the worst – the second worst.
4. Don’t call me after a first date and tell me you are not interested in a 2nd date if I didn’t call you for a 2^nd date. Makes for a very awkward conversation.
5. Don’t be more than 10 minutes late. You will impress a guy infinitely if you are there on time or there before he arrives. Most my dates have been late. In LA, you gotta give people the ‘LA 10′ (10 for traffic, parking, valet)
6. Mouthwash right before a date (like 10-15 minutes before). Buy a travel bottle of Scope, pour it out (it’s alcohol based and just masks the stink) and replace it with the blue Crest stuff or BreathRX and keep it in your purse or car.
7. Don’t try and kiss a woman in front of a subway enterance / exit – you will almost get trampled. And it will be awkward.
8. Always keep gum or mints on your person. When I break out gum at the end of a date, I think it acts as a hint I will try and kiss her.
9. Keep a GasX in your wallet.
10. Keep an emergency $20 – 40 on you (surprise parking garage fees / or in case you have to cab it home)
11. And get Triple A. You will need it or your date will need it (you can call for your date – as long as it’s you have a Triple A number, they don’t care whose car they have to tow)