Desperate times call for desperate measures. Except women can smell the putrid scent of desperation from miles away. It’s bad business sense to ask an investor who turned you down: “Thanks for your time…but can you recommend  some of your other rich friends that would be interested in this venture?”

Sames goes for dating. Why in the world would you ask a person who just turned you down: “Thanks for your time…but can you recommend some of your other hot friends to me?” If you’re a cool cat, I’ll suggest that anyway. But the reason I probably said no in the first place is because you came off creepy & douchey. Asking me to set you up with my hot friends just confirms the fact you’re both. Don’t do it!

Him: Filipino women are very beautiful.

Me: That’s nice…if I was Filipino.

Him: Ahh…well…mixed race women as well…

I’m entertained at his faux pas, and let him continue to shove his foot in his mouth.

Him: Are you a racer?

Me: No, I just pretend to be one sometimes, for fun.

Him: Oh well…I was asking because my friend is an Indy 500 racer. I attended this past year and sat in the $10,000 box. I also own property nearby, but I’m renting right now in Walnut Creek because I haven’t found new renters in this economy…I sell real estate for a living, it’s quite lucrative with all the foreign money from other countries.

I hold back the eye-roll moment at the explicit mention of a big number, high-roller lifestyle. My pause in conversation signals to him that he’s slowly drowning. He whips out the big guns:

Him: You know…you’re very beautiful.

Me: Thank You.

It’s difficult to purposely not smile when any slice of bread tells you that you’re beautiful. I know it’s generic, but they’re still magical words — effective when used once and insincere when used repeatedly.

Him: Do you have a boyfriend?

Me: I’m in between boyfriends at the moment.

Him: May I have your number?

Me: Another time.

Him: I sense you’re getting cold feet?

I examine my own breath, as I exhale deeply into the air:

Me: It’s a very cold night.

Him: I respect and understand your decision. It’s been wonderful chatting with you…

Even douchey lifestyle-dropping not-right-for-me bread can be respectful. I had no idea the two could mutually coexist.

I landed myself a seriously crazy blind date. However, a half-hour before our scheduled coffee date I received an urgent text message: “Call me, please!” It’s never good sign when the first words out of his mouth are: “I’m sorry…” I was being stood up by a boy that had never even met me! He apologized profusely and pushed for rescheduling everything one week later. I accepted because deep down, I believe everyone should be given a second chance.

When he called a few days later for a “getting to know you” phone conversation, I started to believe he had gentlemanly potential. There are several taboo subjects that the majority agrees are “off-limits.” Typically, it’s a good idea to stay away from the heavy hitters: sex, politics, and religion. After cordial pleasantries were exchanged: “How was your weekend?” He launched straight to the meaty stuff: “I believe Americans are a sexually conservative people. In Sweden, it’s common that children talk about their first sexual experience with their parents…”

I thought the topic was an odd choice, but I played along until: “Americans should travel to other countries because they’ve really got it together…and San Francisco isn’t as creatively conscious as…Los Angeles. If you really want to do creative work, you should move to Los Angeles. It’s a socially stifling atmosphere up here in the Bay Area, girls who dress provocatively are labeled as sluts, whores, and hootchie mamas.”

It’s rare that I have to ask this question in the dating process, but I had to whip it out: “Do you LIKE America?!?”

Because not liking America, that’s a dealbreaker.

San Francisco is a small town, approximately 7×7 square miles. You stand around long enough and sprinkle in some time — you’re bound to run into someone you know. That someone might even include an exboyfriend whom you haven’t seen in a year. I knew it’d happen sooner or later the same way I know that I’m going to be questioned the moment I shovel food into my mouth.

When I let my hair down on weekends, I lean towards the artsy indie rock hangouts. Earlier this month, a fashion / music / dj extravaganza at Mezzanine landed on my calendar. Statistically, I had a low chance of running into the ex because simply put: I was the creative and he was the suit. But fate likes to play dirty and roll around in the mud so there I am double fisting two drinks, one in each hand, when I feel a tap on my shoulder: “Hey…you’re looking good” he said politely — with a degree in Urban Sociology, he’d always been one of those people that knew what to say. But when I’m unprepared and tongue-tied, I head straight towards conversation skills 101:

• Graciously agree “Yea…”
• Say the same basic phrase by switching a few words around “…you’re looking pretty good yourself…”
• End with a question, so the conversation ball isn’t left in my court “…still working out at the gym everyday?”

I quickly ran out of cordial & courteous conversation so I introduced him to my friend standing beside me. The next day he im’s me outta the blue: “So…your GIRLfriend seems nice…” Because that’s how boys think: If you’re not into him, you’re obviously a lesbian.

Even thought I might date less in cold weather, it doesn’t mean I’m meeting fewer people this time of year. Because holiday season = holiday parties. That means wiping the mothballs off that shamefully tight cocktail dress and crashing any holiday party I can.

When I’m meeting new people, I usually opt for the easy kosher answer — a handshake. Mainly because it works in all situations and equally well for boys and girls. So it surprises me how many people can not give a decent shake to save their life. Like your appearance, it’s a form of non-verbal communication that speaks volumes about your personality. A limp wrist leads me to believe that other appendages suffer from the same malady. In other words, keep a stiff upper lip and strong firm hand — they’ll be none the wiser. On the other hand, a crushingly tough hand conveys pure hostility and not in the cool confident alpha sorta way.

And if you’re really good you can punctuate the handshake with some yummy eye-contact…while asking me to dance.

There’s a chill in the air. And it’s beginning to look a lot like Christmas… everywhere you go. A little bit of skin is sexy so all the extra bundled up layers makes me feel like I’m coming down with a case of the blahs. I’m beginning to realize that I date less in colder temperatures — maybe it’s a coincidence?

I’m also a workaholic. So it’s a rare occurrence that I go out for lunch, but every-once-in-awhile the fish tacos are calling my name. I head out to the corner taco joint, and patiently wait for my togo order at the nearest open table by the ready counter. Business bread walks past me once, then twice. On the third pass he casually asks if he could share the table — we immediately launch into conversation. He offers me his chips & salsa! Score!

My number is called over the loud speaker. But I ordered my food togo! I couldn’t think of a single plausible reason on how I could take my togo box and sit back down with business bread for lunch. Because…what if he was just a normal friendly boy that liked conversation? What if I overstep his invisible boundaries? But rules were meant to be broken…I should have flashed my megawatt killer smile and said, “Yea…I’d like your salsa all over my chips.” But I get cold feet too.

I’m constantly trying to sharpen my skills — in work, in play, in life in general…so when one of my favorite bread buddies asked me to join him in a networking event, I said, “Sure. Count me in!”

Networking events are a lot like speed dates — you’re trying to leave them wanting more. So when a stringy-haired, pony-tailed piece of bread asked me what I did for a living, I said, “I design.”

He gave me the classic head-to-toe once over, “You design fashion?”

I shook my head, “I used to design for casinos in Vegas.”

A slow cheshire cat-esque grin spread across his face, “You must design the cards people hand out on the strip?!?”

All emotion drained from my face because I do not design soft core porn. And for the record, I do not design hard core porn either. The dense piece of bread misread my flatlined features for quiet confusion and continued, “You know…the cards…that say girls Girls GIRLS!!!” He was one jazz finger away from breaking into song and dance.

A glorious piece of undiscovered bread emerged from the sidelines, “Hey man, quit it. That’s not cool.” He had watched our entire exchanged and felt it was necessary to jump into the conversation.

So while I still don’t believe in prince charming — I believe in knights.

I get approached by strangers semi-frequently. I have no idea what the typical average is, but mine hovers around once every couple months. So, when I was propositioned three times this past week…that blew my average right out of the water! It sunk my battleship!

This makes me think I’ve begun to master the art of looking nonchalantly “available”. And while 2:3 invitations were about job opportunities, there must have been something in my nebulous aura that said “I’m available — Hire me”.

The third incident happened during an intense Sunday hula hooping session. He smiled my way and apologized for not flirting correctly with me. I was intrigued…or maybe I was smitten with his bare-chested topless self decked out in a pirate’s hat. Yep. I can never attract the normal ones. However, at the time I thought he was feeding me a line. It was only until he ran down an entire city block to catch up with me that I realized: this boy must really want to get to know me. I didn’t need to give him my number. After exchanging a handshake, name, and smile, he tracked me down on facebook.

That’s pretty neat. At least I don’t suck at projecting availability.

A few months after my last major breakup, I received some blunt advice “Get back to your date weight.” I don’t think anyone would ever mistake me for a heifer, but somewhere in the span of the relationship I let myself go (a whole five pounds!). It sucks, because it’s usually the girls that put on weight after getting hitched.

I’m pretty lucky. For the most part my weight has been relatively stable through my adult years, and now that I’m sexy, single & ready to mingle, those five pounds somehow magically disappeared!

But the term “date weight” takes the form of many names. Among some girls it’s also known as the “Hey baby” weight. It’s different for every girl, but it’s the size & shape you achieve when random people on the street eye you once-over and yell “Hey baby!” Within San Francisco, the homeless like to use “Hey pretty lady…” because even the bums are classy like that.

The film maker of my original speed dating adventures decided to open a shop of his own: Zoom Dating. Since it was the first event and people can be flaky (not even the good-for-you raisin bran kind), he contacted me (and a few other single friends) as guaranteed eye candy with great conversational skills!

Nine dates total. Three minutes each. Let me tell you, three minutes is FAST. That’s enough for ONE person to give you a reader’s digest version of their life. So instead of asking myself: Would I date this boy? Does he make my mouth water? Do I get warm fuzzy feelings like walking through a bakery? I turned it into something more along the lines of: Would I ever want to have a conversation with this person again? Circle YES or NO.

You’re supposed to receive your “matches” through email the next day…
At 10:30 pm, I started wondering:

• 10:30 – hmm…it’s getting late
• 10:45 – maybe he’s sending the emails alphabetically by first name
• 10:50 – OMG, what if I don’t even have any matches?!?
• 10:52 – …that would explain why I haven’t gotten an email!
• 10:55 – I’m losing my hotness.
• 10:58 – The world is ending.
• 10:59 – *ding* You’ve got mail!
• 11:00 – Hallelujah! 100% success rate
• 11:03 – I’m bringin’ sexy back