Monday, January 31, 2011

3 Things NOT TO DO on a First Date (and 1 Good Conversational Tip)

As much as I have my victories in the dating arena, I don’t want to paint the picture that I’m suave 100% of the time. It’s actually more like 90% of the time, and here is a moment from the other 10%...

At 8:00 p.m. I sat at the bar of Café Ugo, a place I’ve always recommended for an interesting, low-key first date to meet up with an attractive woman named “Maria.” We had met two weeks before at a friend’s birthday party and rather than ask for her number in front of her family, I went a more indirect route and asked for her email address. After going back and forth over a few messages, we decided to meet for a date, starting off with some coffee and dessert, and if the night was going well, we would check out a few other hot spots in downtown Culver City.

While waiting for my date to arrive, I passed the time talking with Ugo himself, a bald, energetic Italian. Always friendly, Ugo wanted my opinion on a new flavor he had created, raspberry cheesecake, which was very tasty. As I enjoyed each spoonful, I hoped my date would arrive, catching me at a nice moment with the restaurant’s owner. Alas, life is not a perfectly timed romantic-comedy, and she called me to signal her arrival as Ugo left his restaurant to check on another one in Santa Monica.

Wrapped in a black winter coat, leggings and boots, Maria looked stylish and pretty. As you might remember, I get excited when a girl I haven’t seen in a while wows me once again with how attractive she is. Next it was time to see if there was chemistry.

Sweets and Coffee

As we sat down for some dessert, we lightly chatted about cooking, family and the like, nibbling at a piece of cake during the idle moments. As I sipped my cappuccino, I could feel the caffeine energizing my body. Maria was a bit reserved and while I’m a talkative guy, I made sure to do the following:

The Conversational Tip: Embrace the Pause

On a date, people feel uncomfortable when there’s a silence and they often try to fill up every spare moment with conversation. That extra chit chat is unnecessary, and if you keep talking, you will probably exhaust yourself. Instead, if you and your date have just finished a topic, let a pause sink in. See how your date reacts as you take a moment to sip your beverage. This gives them a chance to bring up a topic that interests them, rather than you hogging the conversation.

Pauses don’t have to be awkward, and they’re actually nice moments to relax, take in your environment and enjoy a lull.

After an hour or so of having coffee and dessert, the night was going well and I suggested we grab a drink at the Culver Hotel. Nodding her head, we strolled into the night.


Inside the Culver Hotel’s lounge, I was hoping Maria and I could sit on a couch because it feels more intimate to chat sitting next to one another. Instead, we were placed at two chairs 90 degrees from each other, which seemed more fitting for two guys smoking cigars and talking about business and fantasy sports teams than for a man and a woman on a first date. A glass of chardonnay in her hand and a dirty martini in mine, we relaxed and let the conversation wander, as alcohol liberated our tongues.

It was at this point, I made one big mistake, that put a strain on an evening that was going well.

Mistake 1) Do not be too physically flirty

I “slyly” moved my chair so I would be closer to Maria and able to flirt with my hands, as I lightly touched her shoulder during the conversation. Generally, it’s good to initiate some physical flirtation to convey a little fun, romantic interest. After all, if you just sit and talk for two hours, that is something that friends do, and once you’re in the friends zone, it is very hard to be cross over to the I’m-romantically-attracted-to-this-guy zone.

However, my mistake was that I flirted too much, which is a turnoff. It’s better to flirt a little and then see if she flirts back. That’s what chemistry is all about.

We ordered another round of drinks and were having a good time. It had come up that we both like hip hop music and dancing, so I suggested we go to Rush Street, a hip lounge with a dance floor on the second story. I waived down the waiter for the check.

After what seemed like 20 minutes later, I received the bill. In the most relaxed way I could manage, I signed away $50 for FOUR DRINKS. I had broken my own rule of keeping first dates economical, simply because it’s not practical to spend a lot of cash on a first date with a girl that I might not even be compatible with.

Mistake 2) Plan a first date that is economical You should have a game plan on what you will do on a first date that doesn’t require spending a lot of cash. I blew a decent amount of cash on coffee and drinks, which could have spent doing any number of other amazing activities that are more fun and engaging, like seeing the Griffith Observatory or the Getty Villa. Many a men have spent too much money on dinners only to find out by the third date that the girl is not interested. Be creative and practical. Otherwise you’ll spend $70 in one night, which for a 20-something on a budget, is a good junk of change.

At Rush Street, we headed to the top dance floor. I like to dance, and thought it’d be fun to get our groove on. To my delight, it was fun after the first song, then the second…but less so by the third. By the fourth song, we had danced and grinded, but I didn’t feel much physical chemistry. I was dancing with a girl who just liked dance, independent of whether I was there or not. It was nearly midnight, and we had been going out for 4 hours, which brings me to my last point:

Mistake 3) Keep a first date short and sweet. Two hours is a perfect length of time for a first date, and three is ok if there is a lot to do (like going out to a café and later a nearby museum). You can damage a girl’s interest in you by dragging out a first date. A speaker or good comedian always leaves with the crowd wanting more, and you should do the same for your date, so she’s excited to go out again.

Instead, Maria and I danced, even after I was tired, until the lights came on at 1:30 a.m. I walked her back to the car, and headed home beat after a five-and-half hour date. When you’re with a big group of friends, there is so much energy and activity that it’s easy to lose track of time…but it’s a lot harder to spend sooooo much time with one person that you barely know!

Needless to say, the date did not lead to a second. Overall, I had a good time, despite the mistakes I made.

So remember on the first date: Don’t be too physically flirty, be creative to maximize your budget and keep the night short and sweet.

Readers, what mistakes have you made on a first date?

Monday, January 17, 2011

Two Really Fun First Dates for under $40

Remember how I always say that a first date should be fun and inexpensive? Even if you’re unemployed, there is no reason not to go out (which I’m sure you’re already doing), meet a cute girl and then plan a creative and affordable first date. This coming week I’ll be going on two, great first dates.

First Date #1: Local concert and a drink

At a college alumni mixer, I met and hit it off with a cute, playful fellow alumni. Instead of getting her number, I chose to progress things in a different way and one that suits my talents. I’m a good writer, so I befriended her on facebook, and got to know her better through back and forth messaging. Eventually, I told her we should meet for drinks and then asked her for her number. Now I have a really good idea of who she is and what we have in common, so I was excited to send her a text message inviting her to go to a local concert called LA Unheard that features indie rock bands that are on the cusp of getting big. It’s only $10 a person and I’ll spend another $5 for parking. At the concert, I’ll order us two beers, which will probably cost $10. That’s a whole night out from 7pm-11pm where we get to see a rock show and chat over drinks for $35.

I would go to this concert even without a date, and I’m looking forward to it because it’s something new to me. Sometimes on a first date, us men choose to go out to a lounge or restaurant that we’ve been to many times, which is less exciting for us even though it may be thrilling for our date. I think it’s better to plan a date that is new and exciting for both people, so you can share a new experience together.

First Date #2: Gelato Adventure

For another date, I’ll be meeting up with a girl I met at a friend’s birthday. We talked about Italian food and I mentioned there’s a new gelato shop called Grom which is a popular brand in Italy that just opened a store in Malibu

I suggested we go out for gelato on a weekend afternoon, and called it a “gelato adventure.” I mean, who wouldn’t want to go out on anything that’s lableled an adventure? We are going to meet at a Café for a coffee ($8), then take one car to Malibu. We’ll enjoy two gelatos ($10) and definitely walk around the beach on a beautiful winter day in Los Angeles, where the temperature hits a lovely 80º.

I have dinner plans that evening, so we’ll only be able to hang out for a few hours, which is PLENTY of time for a first date. Plus, the more activities you do the better, because it makes the experience seem grander, as opposed to spending two hours at one restaurant for an $80+ dinner. I could stretch that $80 into two, fun first dates that includes live music, the beach and fresh gelato.

Both dates cost less than $40 and will easily take up 3 hours, with plenty of cool things to do so we won’t have to just talk and talk and talk and exchange verbal resumes. I’d rather hear her opinion about the pistachio gelato we’re experiencing, and get to know her over a longer period of time.

There you have it, two perfectly orchestrated first dates!

For my next post, I will reveal the complete opposite of these ideas, a first date I went on where I spent way too much money and stayed out for way too long. Guys, live and learn from my mistakes and successes, that’s what I’m here for.

Sunday, January 2, 2011

Reflections on a Year of LA Dating

If you aren't keeping a dating journal, now is the time to start. In the last post, we saw that dating is very similar to applying for a job, but instead of a career you get a relationship. Here’s another important concept: dating is a skill, and you can only improve through practice and learning from your triumphs and mistakes.

If you wanted to build muscle with a weight-lifting routine, you would keep a log of how many pounds you lifted and for how many repetitions. Over time you would track your results and feel accomplished with your steady success. Dating is the same, but the goal is not bigger biceps, but a boyfriend or girlfriend.

New Years: Life changing night or just another party?

I found myself on New Years Eve at Club Rehab, a DJ school on the west dressed up for the night’s theme “World Festival.” Looking sharp, I had on a fitted white-collared shirt, skinny black tie in a Half-Windsor knot, black blazer, tan pants from Zara, black shoes and an extra element for fun: a blue t-shirt with a large “Italia” printed on the chest. For the night, I was representing Italy by talking to people in Italian, discussing the finger points of “la vera pizza” and, for any lovely females, initiating a European kiss (which is planting a light kiss on both cheeks) right after saying “Ciao!” Spend enough time in Europe, and you will begin to love this delightful tradition.

My friends and I crowded the dance floor as the DJ started the countdown to midnight, and when he yelled out “2, 1, Happy New years!” we happily clinked our plastic cups filled with champagne. Guys were hugged and girls were kissed. Everyone was bursting with joy, surging with confidence from wearing their most attractive outfits, gulping down Patron margaritas and pulsing to Usher’s “DJ Got Us Falling in Love Again” all the while surrounded by new and old friends.

After a few glasses of champagne, the elated feeling I had began to fade when I realized New Years is just a party. It is a fun way to spend Friday night before it turns into Saturday morning. Despite a lot of hype, life doesn’t change after midnight. The idea of creating “resolutions” is ridiculous, because a real goal should be created any day of the year that you’re ready to better your life.

One nice thing about New Years is that it forces people to reflect on their lives, which is something they should be doing 12 times a year, rather than just once. I reflect on my life and goals daily, using a journal to keep track of the good, the bad and the ugly. The failures are especially important to chronicle because they allow you the precious opportunity to LEARN SOMETHING.

So if there is one thing I can encourage you all to do, is to buy a pen and a 10.5” x 8” notebook, with a nice cover, preferably hard-bound. Regular notebooks are simply not built to handle the glories of your love life.
On the front page, right down a goal, like going on one new date a month, and then note how you will work on this goal on a week-to-week basis, such as by planning to attend two social events that will have new people that you don’t already know, each week.

In a way, this LA Dating Blog, is just a public forum of excerpts from my own journal, so that I can share with you what I’ve learned as a 20-something with significant dating experience. I’ve learned things like the following:

Great Idea: For a blind date, I took a girl to the downtown artwalk and had a fun time because we were always moving around and finding visual stimulation to chat all the time. Plus, unexpectedly running into three groups of friends bumped up my social value, which is always nice. J

Not so great idea: On a first date, I made the mistake of being too aggressive with physical flirting, like repeatedly touching a girl’s shoulder or elbow. Lesson learned: a little goes a long way, and learn to read her signals. After all, it takes two to flirt. That’s what chemistry is all about. (This will be the topic of my next post, so stay tuned)

With your dating journal, avoid overanalyzing by just writing what you feel in the heat of the moment, and then studying it the next day. If there is anything you’re unsure about go to two resources:

1) A good friend who is successful with dating or attracting the opposite sex. Avoid sharing with friends who are less experienced because it’s akin to asking a fat doctor on how to be healthy

2) Seek dating experts online, and read their free articles on whatever you’re curious about.  If you type into google “kissing on a date” you will find a lot of great articles from experts with years of experience who write for everything from to The Huffington Post.

If this post has got you to reflect on your dating life, then ask yourself this question and comment below: What have you learned over this past year of dating that you’d like to share with the LA Dating Blog?