the pick-up artist

“I don’t understand the whole dating thing. I know right off the bat if I’m interested in someone, and I don’t want them to waste their money on me and take me out to eat if I know I’m not interested in that person.” – britney spears

i was searching for a quote on dating to use, something profound from say plato or picasso. i ran into ms. spears’ quote and it made me ponder, as the great philosophers often do. is this the view most females take? fiduciary concerns aside, do we always know “right off the bat?”

i had a business lunch with a friend today, we went to an upscale, local restaurant in the town i live in. i’m about 20 minutes outside san francisco, in a beatiful, wooded area with a population that is skewed slightly older, or at least slightly more married. therefore, unless i want to go to the city and spend my hours lurking in cafes and bars, i have very few opportunities with which i come into contact with someone who appeals to me. during our lunch i noticed the other waitress in the restaurant, and was instantly struck by something. mostly it was the way she looked, because unless i was judging her balance or her ability to remember all the orders of a six-top, i didn’t have much else to go on.

let me just say, that i have not been on a date in the last year plus, since my loving ex-wife and i split. one of the main reasons is that we were living in the same house until a couple months ago. Since then, though, as there started to be the room for something, there just hasn’t been the opportunity. work, writing, masturbation. there’s only so much time in the day, not to mention the fact that i’m with my kids from wednesday to saturday.

so i’m checking out the waitress in the restaurant while trying to focus on what my buddy is saying about the idea i just shared. now, telling you about this makes me think about another of the quotes i read a few lines down from britney’s koan:

“I prefer ordinary girls – you know, college students, waitresses, that sort of thing. Most of the girls I go out with are just good friends. Just because I go out to the cinema with a girl, it doesn’t mean we are dating.” – leonardo di caprio

i’m hoping this quote is from when he was much younger, because i’d like to think better of leo. but it made me wonder what ordinary was and what dating was. the waitress and i kept making eye contact, but it was hard to tell whether it was the “waitress glance” or the glance of someone who is checking you out. and i wondered if she felt the same quandary, “is that just the ‘i need a waitress glance'” or is he checking me out. i couldn’t tell what she thought about the whole thing. i was invested in the conversation and spent most of my time involved in passionate discussion. But my mind wandered from time to time, and our eyes met.

i tried to distill if i was attracted to her. whether it was the kind of attraction that would survive a prolonged glance, a dinner, a jaunt to the cinema. what if she was just friggin’ crazy or realized how crazy i was? i started to look at her for clues, trying to guess at the few descript details she had. Analyzing what a ring on her thumb meant and how that would play into her personality. she was wearing a lot of make-up. is that cause of her job, or is that just her bag?

it drove me a little nuts, but it was not without its fun. i decided as the bill came that i was gonna be cool, walk up to her and say “hey, i know you’re in the middle of your shift, but i just want to know if i can take you out. sometime. anytime.” is that wrong? i mean, i haven’t tried this in a while. i don’t remember ever hitting on a girl out of the blue. how else though? with so few, apparent choices that click for me, how am i to strike oil without a little digging. (apologies for the poor analogy)

i plan to head to the bathroom and casually pass by her as she’s ringing in an order. i’ll deliver my message and somehow collect her info without causing a scene. only problem is, we get up to go and she’s gone. i stall for a few seconds. still nothing. so i go to the bathroom figuring i’ll just invert my plan of attack and catch her as i come out. it strikes me, as i’m standing at the urinal pretending to pee, that there is a lot of maneuvering here. is this normal? is this the way shit gets done?

i exit the lavatory after inexplicably washing my hands. i see her this time, but she’s taking an order, a big order and i’m just sort of marooned in the middle of the dining room. i feel people are starting to stare at me, the cooks, the hostess, the patrons; wondering what i am doing standing there, helpless.

then out of nowhere, the waitress who was helping us comes up to me “did you need anything?”

“uh, yeah, i mean, uh. i think i forgot something at the table. she calls across to the busboy who is at this moment clearing my table. he says he hasn’t found anything. she’s nowhere to be seen, but my time is done, unless i want to look very awkward (more awkward than i already am).

i flee.

i’m walking towards my car and playing the whole thing out in my head. “dude, what are you doing? get back in there and be cool. like fonzie. you don’t see pretty girls without a ring very often in this hood” i want what they have to offer and i’m willing to do what it takes. cut to the jennifer lopez quote that makes me realize, in hindsight, why i want to do what it is i think i have to do to get what i think i want:

“If you kiss on the first date and it’s not right, then there will be no second date. Sometimes it’s better to hold out and not kiss for a long time. I am a strong believer in kissing being very intimate, and the minute you kiss, the floodgates open for everything else.”

so i decide to go back in. i use the ideal cover story with the hostess who says, not a little snarky, “back so soon?”. I tell her i forgot to purchase one of the chocolate death cookies, for which the restaurant is famous. I make my way to the back deli counter, scanning the room. she’s not on the floor.

then i see her. she’s sitting at a table eating alone, clearly on her break. I walk up to the table unsure about what i’m doing, if not why i’m doing it.

“hi, i’m sorry to bother you” she looks up, slightly startled, smiles and shakes her head.

her mouth is full and she can’t talk. there is a strained look on her face, just below the surface. i can’t tell if it’s because her mouth is full or if it’s because i’m bothering her while her mouth is full. either way, i have already totally fucked up what i wanted to say. i said ‘sorry’, bad choice of words, i am no longer a dashing man, taking the world by the balls. i sound like a customer. i continue and i feel regressed to thirteen at some cotillion or bar mitzvah, “i was wondering if you’d like to go out with me sometime?” holy shit, did i just say that? i want to melt away. not cause i’m embarrassed by this girl, but because i’m embarrassed by me.

but before i can run she says “sorry, i have a boyfriend.”

i can’t help but feel there is a modicum of dismissal in the way she says this, regardless of the smile she wields. “i apologize.” is what i remember saying. i hope it’s not true, i hope i didn’t say that. but i think i did.

i felt rejection the rest of the day, until all that was left was the satisfaction that at least i had tried. i asked a girl out for the first time in more than 12 years.

so i don’t know if i’d agree with britney or leo. i definitely wasn’t sure i was interested or could be interested “right off the bat” (other than the ‘built-in’ interests) and was she “ordinary” because she was a waitress? i’m not sure, i’m not sure what that means. from my limited experience, the waitresses i’ve dated have been the least ordinary demographic.

either way, i’m pretty sure i was destined to ask her out and she was destined to say no. we we’re soulmates, anti-soulmates. a necessary balance in earths sacred geometry of social interaction. opposing forces creating opposite motion to keep things rolling and keep my world view in check. i love someone already, somewhere, someone i might not know. i wonder what she’s doing right now? i wonder if she’s doing something, at this very moment, that will end up being a zany, ice-breaking anecddote she shares on our third date? the one where we finally have the kiss that j-lo speaks of.

i think the last quote that i found sums it up best:

“I’m dating a woman now who, evidently, is unaware of it.” – Garry Shandling

am_dinerphoto by: Robert Frank, Les Americans


  1. Thanks for sharing. It has never worked out when a guy has tried to ask me out that way. That said, I’ve never gone out with a guy who has asked me out that way. Also, it assumes sexual orientation…since you don’t know anything about the person except how they look and dress.

    And about knowing right away or not…I think it depends on the person. I rely on intuition, and I know usually right after the first conversation if I’m into someone or not.

  2. i appreciate you sharing, as well. it’s always good to hear your pov.

    it brings up an interesting point, though. is there a limitation to who we engage and why? do i only engage those with whom there has been some sort of formal introduction or engagement. is the approaching of unknown entities limited to places or situations that are established as being an appropriate setting for such engagements (bars, parties, etc)? that seems a rather dreary prospect.

    do i have to do enough data gathering on someone’s sexual preference or availability in order to approach? that would seem like a lot of limitations, where enough limiting factors already exists. plus i am not a stalker or a PI and would feel that an irrevocable amount of spontaneity and/or passion might be lost in that type of approach.

    a case in point: i have met beautifully unique, artistic and passionate people through digital means. not least of all you, kristen. if we hadn’t reached out to each other in some way, for example, we would have passed each other by. we would miss out in sharing engagements such as these. granted we are not dating, and i don’t want you to confuse my intentions here. i am thrilled/honored to have a stimulating, if virtual, dialogue and relationship with you. but if you didn’t live in another country would it be outlandish if i asked you on a date. you may not be interested for one reason or another, but is it safe to assume that it would be acceptable in asking? is the real difference, why this would be theoretically acceptable, that we have an identity and some context of each through our writing/communication, that pre-existed? i don’t walk around with my poetry and verse pinned to my clothes. so it would be hard in the physical world to gain the type of context that you can in the virtual world. transversely, it is hard to overcome the physical limitations or proximity of the virtual world.

    on a certain level, i feel as if the people i come into contact with in my world (virtual or physical) are actors or players in my theater and vice versa. it’s karma, to a certain extent, whether they are an extra, a supporting role or one of the leads. it is all in how the script is written and the scene is directed and who the director is. i guess is up to your beliefs in how destiny is manifest, or if there is such a thing.

    it’s my experience that i know the people i want to know better in the first five minutes than i’ll ever know about the rest. so i agree with that part, but how we gain access to those first five minutes is more my issue at hand.

  3. I guess I’ve always ended up with people by not looking for them. I’ve never been a dating type. I’ve always refused being set up on dates, blind dates, etc. Not my

    By all means ask people out spontaneously, but I think it comes off in a certain way to a lot of people. Unless other words are shared previously, it can catch a person off guard. And about data-gathering…it just saves you a lot of time. :) As an experiment…Do you know my orientation?

    And after moving from one relationship to another for most of my adult life, I’m making a concerted effort to stay single. And it is wonderful! I realized how afraid I was of being alone.

  4. Just catching up on your writings. My suggestion: a calling card. This sometimes forgotten little item, that was once done in hand written calligraphy, and used by upper middle class to the elite, has found it’s way back to life. Probably finding new breath from retired business men, aging housewives and mothers, and others. Those who on one level are advancing into the computer age with an email address, yet still have friends who refuse to come out of the stone age, and cling to their phone numbers, needed a way to exchange their contact information. Alas, we are also at the age that finding a scrap of paper and a pen when we need it, is only made worse by forgetting or losing the paper before we get home. Being the artist you are, have a card made up for just this reason: a chance meeting of someone that you cross paths with and that kicks your karma. Your name, this website, and maybe or not your phone number. Simply hand it to the lucky girl (woman?) and tell her that you are glad your paths crossed. The look in your eyes will say the rest. If she is interested she will find you here. Obviously, you are interested, or you would not have given her the card. In regards to the comment by vesper de vil, my guess is that she is more interested in substance than orientation. Being single does NOT mean you are alone, as she has discovered. xo

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