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 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
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
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
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
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.
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.
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?