Friday, March 5, 2010

The First Date Part 2: A Tale of Two Dates



Lets jump back into that first date with Sandra at Ma’kai Lounge and see what went right and what went…less right.

When Sandra first sat down, she was a little out of breath from rushing to the bar. She had arrived 15 minutes late, but all was forgiven because she looked pretty, primped but not too much. We chatted about running and shared a few stories about our experiences.

The conversation on a first date tends to see-saw between funny bits reflecting on recent events and more revealing details about one’s life. Upon meeting someone new, it’s natural to ask exploratory question: Who is this person in front of me? What are they doing with their lives?

On a first date, questions can feel too much like an interview, so I find it best to keep things light, playful and positive. You can save complaining about what it’s like slaving away for your boss for later dates, but for now play with the conversation. See what her conversation sparks from you and vice-versa.

I enjoyed hearing about Sandra’s amusing idiosyncrasies, like how each year had a “theme.” Last year’s theme was “hope” and this year is “change.”

Sandra had a casual, breezy demeanor and she seemed idealistic and self-assured. At 26, she had graduated UCLA where she had studied psychology, and had worked as an assistant position to some high-brow entertainment type. At the moment she was unemployed while living under a protective blanket at her parent’s Beverly Hills home. She spoke of desiring the perfect job, perhaps at the LACMA or some place that aroused her interest in art. She knew she wanted to work for a company where she would be respected and over-bearing bosses didn’t exist.

Young people can always find something to complain about since life after college has not yet lived up to their expectations. A post-grad either spends too much time at work and has no time, or has too much time and not enough money. It can be a vicious cycle, and the only solutions are to find a perfect job, make a perfect job or marry a rich cougar.

One hour is enough

I have found it true amongst many men and women that sitting down and talking for one hour is long enough with someone you barely know. After one hour I get antsy, and this coming from a guy who likes to talk. This is generally where you have to mix it up and take the night in a direction away from interview questions and resume-swapping.

Once I was on a blind date at the Grove and was having coffee with a lovely young lady with whom I had much in common. But after over an hour of sitting, talking and sharing every story I had in a throw-everything-against-the-wall-and-see-what-sticks manner, I was exhausted and was trying way too hard to entertain her. Plus, I gave away my golden stories too early… the ones that guarantee fits of laughter (New Years in Rome) or showcase feats of spontaneous courage (surviving Napoli at night).

After 60 minutes of chatting, planning and creativity will elevate the evening above the standard date. As the man, you are responsible for the night and setting up logistics. Here are a couple of easy ways to find other things to do:

- Arrive 30 minutes early and scope out book stores, boutique shops or other fun bars. Remember our first game of exploring your city? You now have a lot of cool places to check out!

- Use Google Maps or Yelp.com to scout the area. Find out what other points of interest are around you, but be sure to call ahead to make sure these places are open when you are available.

Bring the fun in a backpack.

One time I met a girl in this very, very far away place from Los Angeles called Pomona. I was excited to meet “Jasmine” after we had first met at a Halloween party where she was stunningly dressed as the princess from Aladdin. Through an error on my part, I thought she was from the San Fernando Valley, when in fact she lived in San Bernardino. It seemed logical to schedule our first date at a halfway point, which according to Google maps was Pomona. Little did I know it would take me 1.5 hours to drive there on a Friday night and for her a mere 45 minutes.

I had chosen to meet her at an art gallery/wine bar called dba256 Gallery & Wine Bar.

After a glass of wine, I proposed we leave the bar and picnic at night at a nearby park. I had come prepped with a backpack filled with a bottle of red wine, brie cheese, baguette, strawberries and a blanket. The park turned out to be one of those suburban parks with a few basketball courts and a playset. We hopped on the playset, setup our picnic and had a good time eating, chatting and playing on the swings.

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A Successful Date

More than any other experience, the first date is built up to be a magical first-time encounter. This person could end up being your soulmate. You never know. One thing I’ve realized is this mindless, ambiguous notion that a date is “successful” if you kiss the girl at the end of the night. I don’t know where the idea came from, but the problem is that it’s too “results oriented,” as if to say that two people can’t have a good date without locking lips or just enjoying their time together.

Results-Oriented Society

In school, work and even sports, results mean everything. Good grades, strong sales or a lot of wins under your belt communicate that you are hard-working and can prove it in actions and numbers. Results show that you’ve worked hard at something!

However this mindset does not sync well with first dates. “Success” should mean that the two of you had a good first encounter and want to meet up again, regardless of if you held hands, kissed or had sex.

If you’re a gentlemen looking for a more meaningful, long-term spark, then move slowly with the girl. Make her wait and crave for the first kiss, because that kiss will be much more memorable than a premature smooch.

And now, a few words on the matter from our dear friend Miss Maka Shepard:

“When asked if a guy should attempt a kiss on the first date, my answer is an exuberant ‘Absolutely NOT!’ Lets look at it this way, a first date can go one of two ways: well, or poorly. If it goes well, and you hope to see the girl again, not going in for the kiss at the end of the night leaves her wanting more, ergo, even more motivation to see you again. If the date goes poorly, then it just doesn't matter how great of a kisser you are, if it's not clicking, then better to cut your losses and move on. On the first date, most girls are on the fence about how they feel about you. By putting her in an uncomfortable place by kissing her too soon, you'll be guaranteeing that she'll think twice about seeing you again.”


On that date with Sandra, we exited the lounge after sitting for 1.5 hours and walked around the Promenade to the parking lot. In front of her car, I lingered, hoping for a kiss. Sandra sensed my anticipation and it ruined any chance of me getting a kiss. Instead, she gave me a European kiss on the cheek, and directly stated that she does not kiss on the first date.

I later thought I would put all I had learned from that date into action when I was out with “Tiffany,” a cute Taiwanese girl with a pleasing face and defined, girlish cheeks. I first met her at a mutual friend’s birthday party, and though we didn’t talk much, there was a nonverbal interest that was shared through the eyes. I didn’t think much of it at the time.

A few weeks later, I ran into her at Air Conditioned Supper Club, a warehouse converted a lively dance hall on Lincoln Blvd in Venice. The bar area is brightly lit and there is a huge dance area with booths lined against the walls. I had arrived an hour before to see how I would fair by myself at a club.

When you’re on your own, there is nothing to do but meet other people. After one or two shaky introductions, my people skills kicked in and I could talk to complete strangers with my usual wit. Later, I unexpectedly bumped into Tiffany, we danced and exchanged numbers.

Coffee and Tiramisu

On a Sunday night, Tiffany texted me to push the date back because of a basketball game on TV. “Really?” I thought. “Did we not just pick a time and place days ago and now you’re acting surprised that something else popped up?”

We pushed back the date by an hour to 9:00 p.m., which upon reflection is a bad time to drink caffeinated beverages.

Up my sleeve for that evening was a tried-and-true date spot: Ugo: An Italian CafĂ© in Culver City. This is one of my favorite places I can walk there from my apartment and it has great Italian desserts, including a Pistachio gelato that will blow you away. Plus, it’s divided between a restaurant and a wine bar, so you can play with what kind of mood you want.

When Tiffany showed up, I got the feeling she wasn’t into this date. Besides pushing the time back, she arrived looking unkempt and I noticed it first in her messy hair.

She tried gelato while I ordered tiramisu, a perfect end-of-the-day treat that with two hot drinks cost me less than $20 for 2-3 hours of fun.

The conversation was enjoyable as we chatted about food, cooking and our lives. I felt more relaxed and in the moment, and guess what? I had a lot more fun because of it!

When we went back to her car, I paused in front of her, letting her feel a little bit of tension. I went in for a hug, held onto her arms for a bit, and kissed her. I kissed her once again a bit harder and she returned it. It was nice, and I was thrilled.

Back to Miss Shepard:

Now, I'm assuming that those of you taking my advice are striving to be the gentlemen of the dating world. For those of you who don't fall under this category, then go ahead, be my guest. Plant a slobbery one on her at the end of the night. But if you hope to see her again, hold off on it. Go with the hug instead. But if you absolutely must have that lip contact, give her a nice European kiss on the cheek. You'll end that first date with better chances of it becoming a second.

So you can kiss or not kiss on the first date, but I learn toward the latter. Read the situation and what you’re both feeling. Go with your gut and see what works and what doesn’t.

For reasons beyond my knowledge, Tiffany and I did not go on a second date. However, I did learn that it’s not the best idea to pitch cooking at your place too early, because some people can take it the wrong way.

But there’s a bigger lesson which is You’ll Never Know Her Story

Most of the time when a girl flakes on you or never calls you back, you might blame yourself, but you should not! For whatever reason it didn’t work out, so take what lessons you can and move on to the next date. I have even found out very, very valid reasons on why the girl did not want to go out with me again almost a month after our first date.

Real life examples:

- One girl I never heard back from had a chronic illness and was not exactly in the mood to date because she had important health issues to deal with.

- Another girl I went out with turned out to be really into a good friend of mine.

The girl is not obligated to tell you anything concerning why it didn’t work out after one or two dates. Her world is full of crazy elements you don’t know about, like maybe an old flame suddenly reignited or she woke up one morning and decided she’s not into Jewish guys because her horoscope told her so.

Move forward and do not expect to know why things didn’t work out. Give her the benefit of the doubt, call her once, maybe twice and if you don’t hear back then you know she’s just not that into you.

Now, I hope you all go out and meet people, as often as possible. Take classes, go out with friends and talk to everyone you want to. Get phone numbers, go out on first dates and enjoy yourself!

Next time we’re going to talk about MAKING PLATONIC FEMALE FRIENDS. What it means, how to do it, and why it’s good for your soul.