How to have an epic first date at a restaurant (with wine)


Sometimes I feel that while toiling to create the depths of this very wine blog, I do not most resemble a wine educator or critic or writer, but a grizzled and twisted piano bar singer, putting his own bizarre twist on the classic standards of his era. As the key-plunking crooner might say to himself, "let's see how we can spice up Fly Me to the Moon tonight," I find myself thinking, "how can I reinvent a subject in the form of a how-to wine guide in a slightly less cringey and slightly more serviceable manner?"


Here goes.


One of my all-time favourites. As a sommelier or a waiter, you know where this is headed before it gets there. You can detect nerves, chemistry, confidence, douchebagness, cattiness, pleasure, disgust, almost before they are expressed by the individual.


The first date. Or the third date. I generally like to skip sequels. Always overhyped.


You should be smooth. Smoother than a fresh jar of Skippy™. But how?


Let's cut right to it. You're doing dinner. I personally am a big restaurant person on first dates. It's not for everybody. I've been in so many restaurants both working and dining, that I am extremely comfortable in that scenario, even if I've never been to the restaurant before. I am also good at choosing good restaurants, places that I know will not interrupt a date, but rather, enhance it. I don't choose vegan joints because if I find out my date is a vegan, the date is all but over.


This is all me personally, with my tongue burning a hole in my cheek. It's essential that before you even THINK about doing a dinner date, that you know where the hell you are going and you have a plan to make dinner go smoothly. Do the opposite, and you might as well be trapped in a pair of very high waisted heavy-steel underwear. For the rest of your life. The choice is yours, my friend.


I could say this list is gender neutral, but that would be a failure on my part to recognize my own status as a heterosexually oriented male. Keep that in mind, take what you like, and discard the rest, as usual.


1. If you're not comfortable in restaurants, do something else. I don't care what it is, just do anything that will make you feel comfortable. If you're comfortable and relaxed, your date will pick up on that, and they'll feel more relaxed. Relaxed people get it on sooner than those who are uptight. Being relaxed and confident is sexy. Being uptight and trying to be confident makes you look like a total douche.

2. You're doing dinner. Start by doing your fucking homework. Pick a place that's going to be busy, or at least have a vibe. Choose vibe over food type, don't worry too much about their preferences. Maybe don't choose pizza or sushi. I mean, you're already reading a wacko wine blog, you must be open-minded. Your date should be, too, and if they're not, get rid of them.

You'll have a reservation, so busy won't be an obstacle. Busy places do a couple of things for you on a date. They give both of your eyes something to look at instead of each other, and they give your ears something to listen to instead of each other. When a room is bustling and there is music playing, it takes the pressure off of you both to come up with interesting conversation.

3. This should have been rule #1, but make a FUCKING RESERVATION. You don't even have to use it. Let's say you get to the restaurant and you see some bar seats open. It's a first date. Sometimes the bar is more relaxed, less formal. Just say, hey, I have a reservation at 7pm for Paul Allen, but is it OK if we sit at the bar? Restaurants are fine with this. It opens a table for a walk in, and they don't lose revenue because you sit at the bar for dinner. Now you have the vibe of a pop-in, but if the place was packed, you'd still have your table. Win-win. Make the reservation.

Sidebar: I will say that the irony of all this conjecture was that the night I met my fiancée, we did pop in to a busy place on a Saturday night without a reservation. We were seated, we missed half of the game I had bought tickets for, and the rest is history. The pop-in was spontaneous, on the way to the stadium for an event, and therefore, if the answer was no for the restaurant pop-in, we were already on the way to a planned evening. Rules are meant to be broken, but break them tactfully or you'll end up with a cold date.

4. Be patient, be polite. A waiter or a bartender can't singlehandedly get you laid, but dammit if they can't help the cause. Treat the waitstaff with the utmost respect. Not just on your dates. In fact, if you can engage with a bartender or a waiter, regardless of gender, it's a good thing. It will show your date that people like you, and that you are a nice person who likes people. It's attractive. You have all night to focus on each other. Smell the roses a bit and engage with those who are taking care of you. Often, it can result in a little treat being sent out or a special offer on an unlisted wine. Once this kind of thing starts happening, you all of a sudden appear to be "the man", and you didn't have to throw your wallet around or act like a big shot.

5. Wine. OK. Finally. You've got a few problems plaguing you at this point. First, you feel like you have to pretend to know something. Well, if you've picked a good restaurant with a good wine program, there will be someone on the floor that knows the wine at the restaurant. Don't be that guy who doesn't ask for directions. When you politely ask for directions, what people see is someone who is comfortable in their own skin, and what you really are doing is asking for adventure.

6. Now, before that, you should figure out if your date even likes or wants wine. You could be on a date with a sommelier for all you know. Let them speak. Get their input. See how they feel. Try to pick up on cues that tell you if this person wants to take charge or if they are OK with you taking charge. Taking charge without being overbearing can be tricky. Personally, as a take charger, when I am combing a wine list, I like to point out when I get excited about one. I almost sell the wine to the date. I'll say, hey, I don't know what you like, but they have a really cool wine that has this, this, and this about it and it's pretty rare. You wanna try some? Their interest should be piqued if you told a nice story about the wine and seemed excited. I'd want to try it. This might help them decide and take the pressure off of that if they were unsure, and that's a relief for many people. You didn't decide for them, but you helped them shed the stress of choosing. Many people appreciate this.

7. See if you can detect before ordering if the person is really and truly open-minded. If you think they are, ask the waiter or sommelier to choose a bottle for you. What could be more exciting than discovering something sensual together? I'm already glistening. Think about it. You have an immediate point of exciting uncertainty which will lead to a shared sensual experience that doesn't require you to creepily place your hand on their thigh in a movie theatre. Totally safe and appropriate.

8. If you do choose the route of adventure but you don't want to get hosed on price, there are ways of discussing this gracefully, even if you don't want to spend much. Keep in mind that a lot of wealthy people out there don't spend a lot of money on wine. You don't have to if you don't want to. It doesn't say that you're cheap. At least if you don't make it come off that way.

When you look at the wine list, figure out what the low-end prices are, and figure out what your cap would be for a stellar and fun experience. The truth is, it's awkward for a lot of sommeliers to bring up the price thing for fear of offending people in any number of ways. You can really make a sommelier's life easy by being up front with them. Don't say, "could you pick something on the low-end?", but use the actual numbers. Say, "could you choose something for us to match the appetizers between $40-$60 roughly?" Hey, $40 might be the cheapest bottle on the list, but your date might not even know that if they didn't look at it. Say it confidently. Do not cower, do not act shy about what you are willing to spend. Be proud in what you are able to spend. Sommeliers who detect genuine interest over flash will appreciate it, and often reward those who who express it. Somms aren't rich, either. They get it, and they want to help you. They probably have some cool cheap bottles that most normals are scared of because they can't come close to pronouncing them. These are for you.

9. I don't know what's cool these days, but I am old-fashioned when I take a girl out. I grab the bill, no questions asked. I try to do it when they go to the bathroom. It takes the awkward conversation and pretend "no, no, let me get it" out of the equation and adds an element of mystery. It's less stressful overall. And it's a surprise. Whether you say you like them or not, surprises that save you money are exciting and harmless.

10. Before you go on your date, you should prepare. Nobody with any sense of idealism likes to hear this, but there are some easy things you can prepare to keep conversation flowing and elicit chuckles and playful conversation. Make it a question that somebody would have to justify, not just say yes or no to. Present a conundrum. For example, you can engage a server/bartender AND your date in a playful conversation by presenting a conundrum. A favourite of mine is the sweater gift problem. You say, "OK, there's this sweater I want to buy for a female friend of mine, but I don't know what size she is." It's like a jar of pickles. Everyone has to chime in. Do you buy the sweater a size too small to be complimentary about her figure, or is that offensive on the backend when she needs a bigger size and it doesn't fit? Do you buy a size large? Isn't that pretty much saying you think they're heavy? What does one do? This will get some laughs going and get everyone involved. You can start with your date and then appeal to the waiter for a verdict. And hey, it's a hypothetical question. Get creative. Watch an episode of Seinfeld before. The show is filled with these kinds of conundrums. There's a reason it's the most successful show in the history of television. Use it to your advantage.

11. Stand up straight, sit up straight, and don't forget to smile. The more you laugh, the better.


And don't be a dick. This is too basic to qualify for the list.


Do these things, then call me and tell me how it went.



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