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The vacation waiter fling

Okay, so I've been talking vaguely about this great vacation fling I had the other week, but I haven't given you all any good details. Also, I promised yesterday that I would talk about the kind of pick-up that actually gets me into bed. Conveniently, these two themes fit together nicely.

I was on vacation, and I was getting hit on a lot, because that's what happens to women visiting beachy tourist spots, but, for the most part, the men hitting on me weren't interesting to me, until my friends and I went to what we'd taken to calling the restaurant with the hot waiters. (All the restaurants on the island are open-air, so you can preview the waitstaff, and we'd been walking by this place for a couple of days and commenting on the cute staff.) So, we got a table, sat down, and started flirting with the waiter.

(Guys, this is a good time for me to mention that if a strange woman is flirting with you, that's a very good sign, but it's not a slam-dunk, so don't get your hopes up just yet.)

One of my girlfriends seemed to hit it off with our waiter, which was fine, because one of the other waiters was more to my taste. (He had these really hot, geeky glasses. Be still my heart!) So, every time "my" waiter walked by, I made eye contact with him and held it just a little longer than would be accidental. Eye contact, we all know, is key in flirtation and pick-ups.

Soon after that, our waiter handed our table over to "my" waiter, and we got on with the serious flirtation. He was friendly but not fawning, attentive but not desperate. It was great. I'm a pretty shameless flirt, and given a responsive partner in flirtation, whether it's going anywhere or not, I'm completely happy. Also, as it turns out, this gets you better service, if the object of your flirtation is a server. We got a free carafe of wine, for example, and our water glasses were never empty.

Ultimately, however, I'm a chicken, so as our meal was winding down, I hit the point where I wasn't going to be able to move things any further along. This is, largely, because I'm shy, and just like anyone, I fear rejection. Luckily for me, as a woman, this doesn't mean I have to go home alone at the end of the night. I know this sucks for you guys out there, especially the shy ones, and I feel your pain. I figured I'd had fun flirting, and that would be that, when our (my) waiter came to the table with a round of complimentary nightcaps and a card for free drinks for the three of us (classy) at a bar nearby. He told us when he'd be done at work and would be at the bar.

Let me interrupt my story for little bit of commentary, here. First, this guy was paying enough attention to know I was flirting with him, and to play it up. He didn't jump the gun and try to invite us out in the first gambit of the conversation, but he also didn't wait until we were actually departing the restaurant. Of course, he had the advantage of knowing we'd be there for a while, which isn't necessarily true of a woman you might want to hit up in a cafe or a bar, but if you know you have plenty of time, using all of it is absolutely the way to go. He was funny and charming, and when the time came to step up and move things from casual flirtation to serious intent, he did it smoothly and without pressure. He was clearly interested in me, but he included my friends in the invitation, which is both obvious and genius. Very few guys do this, despite it being obvious, but it'll increase your odds a lot, because a woman is unlikely to want to go into a strange situation by herself, and also, because it's just good manners.

Now, it turns out my friends couldn't come to the bar because they were getting up early the next morning. (I was on vacation, which meant no plans that involved having to be up before 10am for me.) We told him this, so he wouldn't bring friends along to flirt with my friends, and he and I agreed we'd see each other later. I told him my name and offered him my hand to shake, which he, of course, kissed. This move can be cheesy, but in this case, it really worked, but, then, I'd already decided I'd be sleeping with him later.

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Any woman who looks at me like that immediately turns me into the shyest person in the world.

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