Naked Truth #2: It Doesn’t Always Pay to Pull Out all the Stops on a First Date

Lots of guys think they have to go all out on the first date to impress a woman and get her interested, but the date itself is really only a small part of the equation. When you read my assistant’s story below about her two Tinder dates (and find out which guy she ended up with!) you might consider getting to know someone a little better before you go for broke. -Lisa

Two years ago, fresh out of grad school and single as I’d ever been, I downloaded Tinder. I was tired of hanging around the same guys in the tight-knit L.A. circle I had floated in and out of since college, and I figured I’d give it a shot. In the three months I was on the app, I only ended up going out with two of the guys I matched with… but the dates couldn’t have been more different.

I met the first guy, Robby, for drinks at a Dive Bar of his choosing in Santa Monica. I didn’t feel some over-the-top attraction at first, but I had a good time. He was handsome and intelligent. We spent about 45 minutes together, enjoyed some interesting conversation about music and art, and parted ways. I didn’t know if I would see him again, but there was a quiet confidence about him that intrigued me, and so I checked the box for “maybe” in my head.

My second Tinder date was, coincidentally, scheduled for the following night. (I wasn’t one to waste any time!) Let’s just say this one was a step up from drinks at a Dive bar. Brendan had an “extra” ticket for the sold-out Paul Mccartney Concert at Dodger Stadium. He lived within walking distance of the show, so I met him at his place before the gig. When I arrived, I saw that he had arranged an elaborate wine and cheese spread on his back patio and had cued the new Sharon Van Etten record we’d been chatting about over text on his sound system. It was pretty adorable. When we got to the venue, I was pleasantly surprised to find our seats were top notch— on the floor, just behind third base. “If this is all for the first date,” I thought to myself, as Sir Paul transitioned into ‘Blackbird,’ “what would he possibly do for our second?”

Well…. we never made it there. Brendan was a total sweetheart, and we had a good time together, but as we were walking back from the concert that night, my mind turned—rather unexpectedly—to Robby. Here I was, on this incredible date with this sweet guy who had clearly put a lot of effort (and $$$) into showing me a good time, and I was thinking about the guy who picked the less-than-impressive dive bar for our first meeting? Let’s just say I was as surprised by my reaction as you probably are, dear reader. But, as Emily Dickinson once wrote, “the heart wants what the heart wants – or else it does not care.”

The next morning, I woke up to a text from Robby asking how the concert was. (I had mentioned I was going, but had conveniently left out the fact that it was with another guy I had met on Tinder.) We texted back and forth for a bit, and he asked me if I’d like to have dinner with him later that week. This time, he stepped up his game and suggested a nice restaurant in Venice Beach.

I have to admit, the date felt a little awkward in the beginning. While it wasn’t our first meeting, we still hadn’t had the time to develop any real rapport. We were both too nervous to eat a big meal, so we ordered a dozen oysters and a bottle of wine. The oysters were delicious and I was flattered that he’d taken me to such a nice place, but it wasn’t until we sunk into a comfy booth at another dive bar afterward that we really warmed up to each other. There was just something about a no-frills, no-nonsense spot that took the pressure off and made it easier for us both to relax and open up. (Come to think of it, that bottle of wine probably didn’t hurt, either!)

It’s been almost two years since that date, and eight months ago, Robby and I moved in together. The moral of the story? Sure, it’s always nice to put some thought into a date and make an effort to show someone a good time, but at the end of the day, a date only lasts an evening, but a Real Connection can last a lifetime.

While I don’t necessarily advocate taking a woman to a dive for a first meeting (I still give Robby sh*t for that… a nice wine bar is more my speed!), the next time you feel totally stressed about planning that perfect date for a woman you hardly know, remember—the heart wants what the heart wants. If you have a real connection with someone, it’s not going to matter whether you take her out for a cocktail or to a Paul McCartney concert on the first meeting. Grab a drink! Go for a walk! Make a picnic! Take her to your favorite taco stand! If there’s real chemistry—and your date’s not some totally shallow you-know-what—she’s going to have a good time, and you’re going to get a second date.

Are you having trouble meeting someone out in the dating world? Book a consultation with Lisa and see how she can help you turn your dating around!

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