What to Expect
The Practice
You and the Other Person Agree to Meet
Seems simple enough, right? You think, and you decide that you’d like to go out for a drink and chat. The problem is, dating etiquette is what makes this easy. You have to ask the other person. In other words, you have to message them. Now that you’re having some serious thoughts about this person, you decide, you know what? I’m going to message them first to see what they think. You message them, then they message you back. The whole thing works backwards and forwards like a game of Snakes & Arrows.
Do They Agree to Meet?
Someone you’re interested in dating may agree with your feelings or have mixed feelings, but either way they want to do something about it. They’re the ones who are going to put themselves out there, which means they’re the ones who should. It’s generally much more respectful to ask if they’re interested before you message them first, instead of firing off a message and walking away. If they say, “Yes,” great! You had a positive response, and if they say, “No,” then at least you put your best foot forward.
People vary in their level of comfort with online dating. Some of us are so used to the technology that we feel more comfortable expressing ourselves online than getting out of our comfort zones. Others prefer the anonymity of a text or email. You can usually decide the best way to approach someone after you’ve met them. If you’re meeting for drinks or coffee, there’s an easier way to get things started. If you’re going out for a meal or dinner, you’ve found your match and this isn’t a bad idea.
If you’re leaning toward another conversation over a meal, then just ask about what you’d like to talk about. Maybe you’d both like to talk about your exes, the best vacation you’ve been on, or the most recently-ended relationship you’ve been in. In some cases, there’s nothing you have in common. You can mention something like that or just change the subject, but first you should have a conversation starter you can use to keep the conversation going and to gauge whether the other person would be open to that topic. Of course, this is a general guideline, not an absolute. Use your intuition and you’ll be fine.
The Practice
Failing a Conversation Starter
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I know, it’s cheesy, but bear with me. These are the keys to a great first date.
And since you’re probably reading this article, odds are you’ve been out on a date or two before. So what you’re going to learn from here should be applicable to your dating experiences as well as to the date going on right now. And for that reason, I will keep dating examples specific to the 21st century, something like “a man and a woman went out on a date to a trendy restaurant on the Upper West Side,” for example, and I will use hip-hop references.
So, to recap: Being too chill is a turn off, but not being too chill is a turn off too.
1. The Right Amount of Chill
This seems obvious, but again, bear with me. When you first meet a potential boyfriend or girlfriend, you don’t want to come across as too much of a loner. But you don’t want to come across like a complete party animal either. You want to have a balance: enough chill that you seem approachable, but not so much that you’re totally immune to an interesting conversation. Plus, being too chill can be a turn-off. If you’re looking for a relationship, you want to make an impression. Trust me. If you come across as a party animal, you’re not going to get very far. Similarly, if you come across as a loner, you’re not going to get very far either. Which brings me to the next important factor.
The first impression you make on someone is everything, so you want to make sure that it’s a good impression. The thing is that you don’t have to be a total cliche to make a good first impression. Take Brian, a 24-year-old who lives in Brooklyn and works in sales. He went to a party with his friends the other night and met this woman named Alison in the middle of the festivities.
Brian: Alison was a drunk mess. She talked nonstop. She was about five drinks in and making a mess of her drunken stories. She was loud. She wasn’t listening. She was a total mess.
Me: What did she say?
Brian: I talked to her for about 20 minutes, but she was just all over the place. She started talking about her sister having a nervous breakdown that she didn’t want to talk about, she was talking about her family, and
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