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How to emerge from the digital world and navigate a real first date

A bar sets the scene for a casual

A bar sets the scene for a casual first date. Photo Credit: Flickr / Anthony Quintano /

First dates can be a struggle for both sexes, especially in the age of digital dating. This week, our Tinder experts talk tips on how to emerge from behind your iPhone screen for a successful real-life interaction.

In online dating, who should initiate the first in-person meet-up?

Kelly: Either person involved should feel ok about doing this. The great thing about online dating is that everyone has the same overarching goal: to go on a date. Do I prefer that the guy sets up the date? Sure. But if the back-and-forth small-talk is turning into more of a chore, I'm not opposed to cutting to the chase. Here's how you do it: "Hey, let's hang out this weekend." Works like a charm. None of us are using these apps to find pen pals, and if you are, please log off forever.

Matthew: I see a lot of women post things like, "Message me first or I'll delete you," or, "Chivalry is not dead. Message me first." Honestly, online, and out in the real world, it shouldn't make a difference. If you like someone, ask them out.

What is a fool-proof way someone can score a date with you?

Kelly: At the risk of sounding like a cliche, if you're funny, you've got my attention. Trying to make a stranger laugh through in-app messaging is probably my generation's greatest struggle right now, so when it's done successfully, I lock that guy down right away. Insider tip: "lol" means I'm not laughing and "hahaha" means I'm in love with you.

Matthew: Tell me you'll take me out for pasta, then come back and watch hockey and have sex with me at my place. You said "fool-proof" -- there it is.

What is the best line you've ever used to score a date?

Kelly: Not sure why, but whenever I tell a guy that my best feature is my 401K, the response is overwhelmingly positive. Must be a weird fetish or something.

Matthew: I refer you to the great Taco Bell pickup of January 2015: see here. Not only did it score me a date, but it got me laid. Cheesy Gordita Crunch for the win!

What is an ideal first date setting?

Kelly: I almost always insist on a bar because it eliminates, or greatly reduces, any awkward elements surrounding the night. First, there's always music playing in the background, perfect for filling any gaps in the conversation. Second, you're surrounded by people consuming alcohol, perfect for people watching if you can't think of something to say. Third, you're consuming alcohol, which for me, eases anxiety a bit. And finally, you only have to stay for however long it takes you to finish one drink, giving you an easy out in case the date is turning into a dud.

Matthew: I'm studying for my Bachelor's in alcoholism, so going for drinks works for me. It's also a relaxed setting to get to know someone for the first time. Simplicity is effective here. Don't try and come up with an elaborate first date.

Who should pay on the first date?

Kelly: I'd be a liar if I said I didn't expect the guy to pay. I know, my feminist instincts are yelling at me too! The best way to navigate this situation is if both of you pay for portions of the night. For example, he buys the first round and you handle the second. Or my favorite, he covers all of the drinks and you buy the falafel. Either way, I always make a move toward my wallet when it comes time to pay, as a precaution.

Matthew: Depends on who initiated. If the guy asks the girl out, then the guy should pay. If the girl asks the guy out, the guy should still pay but it wouldn't be ridiculous for the girl to chip in. In either scenario, the girl should at least offer to pay.

How much personal info do you share on the first date? What are topics you should NOT bring up?

Kelly: I'll share all of the basic information, but I also like to get out a lot of my "unpopular opinions," though I stand by them 100 percent. One example is that I think Kim Kardashian West is a genius walking among us simpletons and we all wish we were as confident as her daughter, North. If a guy is still interested in me after that proclamation, we're good to go. I also don't think guacamole is that great. Whoops! Can't give away all of my good material. The one topic I don't bring up is exes. It's not that it makes me uncomfortable, but rather because it's not a very fun topic for a first date. Save that heated and uncomfortable conversation for date number four.

Matthew: I read a date before I see what I can and cannot bring up. Every date is different. Personally, nothing bothers me from a female perspective. I'd recommend not talking about ex-boyfriends, because most guys won't like that. However, when I hear about ex-boyfriends, it just helps me put another piece of the "How do I get laid?" puzzle together.

How do you like a guy to dress on the first date?

Kelly: Casual attire is the best. Since we're most likely going to be at a bar, I suggest leaving the suit jacket at home and opting for nice-fitting jeans and a T-shirt. I'll most likely be putting enough time and effort into my outfit for the both of us, so there's no need for you to drive yourself crazy with such a monumental decision.

Matthew: I like something that shows off a girl's body, partially because I'm a pervert and partially because I want to see that she's confident with what she's working with.

What's a good ice-breaker if the date is off to an awkward start?

Kelly: If you feel that the date is starting awkwardly, address the awkwardness from the very beginning. One time I made plans to have drinks with a guy I met via Twitter DMs -- a weird and unfamiliar situation overall. I knew it and he knew it, too, so my very first IRL sentence to him was, "Hi! [hug] So, how weird is this whole situation, huh?" We both laughed in agreement and the topic wasn't brought up again. If you don't address the awkwardness, you'll just be thinking about it the whole time while he's trying to tell you about his life-changing experience backpacking through Europe.

Matthew: Ask about bad dates the girl has been on. Also, talk about bad dates you've been on. Rather than avoid it, hit the awkwardness head on. Another reason I suggest going for drinks: alcohol helps numb the awkwardness.

So we've established that alcohol is a go-to first date crutch. But how much is it acceptable to drink the first time you're meeting someone?

Kelly: A good rule for drinking on a first date is to remain slightly less intoxicated than your date. For me, my life is essentially a string of embarrassing moments, and gin doesn't help. So when I'm trying to make a good impression and make someone want to kiss me, avoiding any behavior that could be described as "sloppy" is ideal.

Matthew: If you and your date both agree that you just want to go out and get drunk, then it's acceptable to get as drunk as possible. Outside of that, don't get bombed. I recently had a reader tell me that she went out on a date with a guy who proceeded to get blackout drunk, called her the "C-word" (jokingly), and then he cried. Don't be that guy. Ever.

Sex on the first date: Yes or no and why?

Kelly: I'm going to say no. Don't get me wrong, I'm not here to shame those who have sex on the first date. I'm here as an advocate for first base. First base, AKA making out, is the most underrated base and we as a society don't give it the time and appreciation it deserves. Let's use first dates that are going very well to focus on the wonder that is making out. A proper make out session is a lost art, but I think if we try hard enough we can bring it back. Whether we bring it back on the patio of a dive bar in Brooklyn or in front of the Union Square Whole Foods, let's just kiss for now, yeah?

Matthew: Um, yes. Because it's awesome, that's why. Seriously though, that's my reasoning. Sex should be fun for both parties involved, and people should be doing this more often. The world would be a much better place. I think that's going to be my campaign when I run for president in 2024.

Kelly, what was the best touch a guy ever added to a first date?

Kelly: One of my favorite things that a guy can do is take things we talked about on our first date and make reference to them in the days to follow. After my most recent first date, the guy sent me a picture the next morning of a subway ad we talked about. This tells me two really great things: One, he doesn't think it's weird to text back the very next day. And two, he was actually *GASP* listening to me.

Matthew, what is the best move you've ever pulled to get a second date?

Matthew: This is a tough one because most girls usually don't get a second date with me. You all know the story, but ultimately I'd say the best move I ever pulled was when a girl told me she had a kid after our first date and I didn't panic to ensure I got a second date. She did side work as a model; I had to see that one through until I closed.

How soon is it acceptable to text someone after the first date?

Kelly: I'm a big fan of texting and I don't understand why there are so many dos and don'ts involved. If a date went well, I'll send a quick text that night letting him know I got home safe and that I had a lot of fun. If the guy feels this is coming on too strong, he probably wasn't worth the data charge. Playing games like waiting five hours to respond to his, "Hey, how are you?" text gets you nowhere and only delays future dates/make out sessions in front of Whole Foods.

Matthew: My general rule of thumb is to wait 48 hours. Occasionally I've texted a lot sooner -- especially if I know a date's gone well -- but if there's a girl I genuinely like, I'll wait 48 hours. If she texts me before that, even better.

Head to every Friday, as Matthew and Kelly take on the realities of dating in NYC from both sexes' points of view. To inquire about NYC dating advice, email them at Your question may appear in a future column, but no names will be used.


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