Three Easy Steps to the Perfect First Date

I was talking to a friend a few months ago who said he wanted to start doing more fun activities on his first dates with women. Seems like a good idea, right?

Wrong. When you’re on a date with a woman, the goal is not to have fun. It’s to make a connection. And every second you spend looking at or engaged with something else is a second you’re not engaging and connecting with her.

Once you realize this, you’ll see that trying to do something original and fun is not just unnecessary, it’s counter-productive.

So, what’s the fastest way to make a connection?
  1. Meet for a drink and sit at a 90-degree angle to her. Have her meet you at a bar or lounge that is not too loud, i.e. not a sports bar or a nightclub. It doesn’t have to be a fancy or trendy place, but it should have soft lighting and a nice ambiance. Get there early enough to sit at the corner of the bar, or if that’s not available, find a table and move the other chair in such a way so that she’ll be sitting at a 90 degree angle to you. This is important because sitting face-to-face across a table is awkward because it feels like an interview, and there’s a table in the way, making physical contact more difficult. Sitting side-by-side at the bar can work in a pinch, but you have to make sure to turn your body to partially face hers, otherwise you’ll both have to crane your necks to look at each other. (You have her meet you there not just so you can get there before her to choose the right spot to sit, but also because she might not be comfortable having someone she doesn’t know picking her up at her house. Pick a place in her neighborhood if she doesn’t have a car.)
  2. Look her in the eye and have an intelligent conversation. “Intelligent conversation” may very well be a topic for a whole series of blog posts, but the crucial detail here is “look her in the eye”. Most men don’t do this, and that’s why they fail. You can’t connect with someone if you don’t look them in the eye. Eyes are the window to the soul. “Intelligent conversation” doesn’t mean bore her with intellectual topics. Keep it light and fun. Don’t interrogate her with a bunch of questions, and don’t brag about yourself and your accomplishments like most guys do. It doesn’t really matter what you talk about as long as you’re not being creepy or boring. (Turn off your phone and give her your undivided attention. And just to be clear, this is not a staring contest. You can look away from her eyes every few seconds. But they should be your anchor point.)
  3. Hold her hand and escalate consensual physical contact from there. I don’t know what it’s like in other cities, but a lot of women in Seattle have told me how refreshing it is when a man holds their hand on the first date. Apparently, most men here are too passive to make any physical contact at all. Holding someone’s hand is not a creepy, aggressive move. No one has been sued or publicly shamed for sexual harassment because they held someone’s hand. I’ve held a woman’s hand within the first five minutes of meeting her. You’ve held someone’s hand within the first 5 seconds of meeting them, too. It’s called a handshake. With someone who likes you, you can hold their hand a little longer. If you need a pretext, act like you’re interested in her jewelry. Or hold her hand up against yours and say “Wow you’ve got long/short fingers. You’d be really good/bad at playing piano/basketball/whatever”. Gauge her reaction. If she pulls her hand away almost immediately, wait another 10-15 minutes before you try to hold her hand again. If she doesn’t pull her hand back, maybe give her a hand massage.
Where you take it from there is up to you and her. If she’s touching you back and leaning forward and giving you bedroom eyes, kiss her. If not, keep talking. The key is to pay attention to her body language and move things forward at the right pace. Don’t try to make anything happen or put pressure on her. Not only is a high-pressure approach sleazy and unethical, it’s also ineffective. Women aren’t attracted to desperation. But if you show her you’re not in a hurry to have sex on the first date, she’ll be a lot more likely to have sex with you on the second or third date (maybe even on the first date).

Why is this approach so effective?
    Because it’s how women connect – I didn’t know why this worked so well until I read the book You Just Don’t Understand – Women and Men in Conversation by Deborah Tannen. As she says “I found that at every age, the girls and women faced each other directly, their eyes anchored on each other’s faces. At every age, the boys and men sat at angles to each other and looked elsewhere in the room, periodically glancing at each other. They were obviously attuned to each other, often mirroring each other’s movements. But the tendency of men to face away can give women the impression they aren’t listening even when they are.” [1] When you go on a date with a woman, and you think it’s going well because you’re back at your place and you’re making out and then she says “I feel like I don’t know you well enough”, this is why. Because you didn’t connect.
    Because it’s low-pressure and low-commitment – asking her to go bowling, kayaking, or play racquetball invites a bunch of variables into the situation: she has to find the right outfit, she’s tired at the end of the day, she doesn’t want to sweat or grunt in front of you (at least until she knows you better). Dinner involves a lot of complicated distractions: what to order, dietary restrictions, table manners, who pays the bill, etc. When you say “Meet me for a drink”, there’s no awkward concerns about reservations or buying tickets. All she has to do is show up.
    Because it’s cheap, regardless of who pays – for the cost of one or two drinks, you can know right away if there’s a connection or not.
    It communicates confidence – Inviting a woman on a elaborate date says “I really like you so I feel like I need to impress you”. This kind of attitude is not a turn-on for women. “Meet me for a drink” says “I want to get to know you better first to find out if I like you” It sends the message that you know you’re fun and interesting and you don’t need dinner, live music, or any other fun activities to entice her into spending time with you.
    It’s distraction-free – Going to see live music may sound fun, but you won’t be able to talk to each other because the music will be too loud.
    It’s efficient – If you don’t have chemistry with them, you can find out in half-an-hour with minimal expense.

Objections/Concerns:
    “I’m an introvert and this is too intense for me” – I’m an introvert, too, so I understand your objection. Seriously, I hate going to bars and meeting people, and I get really nervous in social situations with strangers. I’ve even pretended to go to the bathroom to avoid getting in the elevator with co-workers! However, if you want to be successful with women, this is a skill you’re going to have to learn. Saying “I can’t because I’m introverted” is like saying “I can’t go to the gym because I’m too out of shape” or “I can’t go to yoga because I’m not flexible enough”. Of course it’s going to be uncomfortable at first, but you’ve got to deal with that initial discomfort if you want to improve. And also, this is someone you like, and who likes you. If you can’t look her in the eye and talk to her, how are you going to have sex with her? If you really can’t picture yourself sitting down, making eye contact, and having an intelligent conversation, then by all means do an activity like walking around the park first to create an initial rapport. But then make sure you follow it by going to a bar or coffee shop and doing the steps above. Practice making eye contact and having conversations in other low-pressure situations on a regular basis. It’s like anything else in life – the more you do it, the easier it gets.
    “This feels like a pick-up artist/seduction technique” – No, it’s not. This is not seduction or manipulation. It’s about creating the right environment for a connection to develop naturally, if the attraction is there. If you don’t like each other, no amount of eye gazing and deep conversation will get you into bed with each other. If, however, she is attracted to you, this is the fastest way to make a connection so she feels comfortable getting intimate with you. And for the record: there are plenty of women who enjoy having sex on the first date, and there’s nothing wrong with that. When you really internalize this fact and get comfortable with it, women will be more comfortable with you.
    “I’m not trying to be smooth and get women into bed” – It doesn’t matter what your end-goal is, your short-term goal is to make a connection. I did this with my girlfriend on our first date, and we didn’t sleep together until almost a month later. But we both knew we wanted a second date because we had allowed the connection to develop.
    “If I do this with someone I don’t like, then I just had a boring date” – I can’t guarantee that you’ll be attracted to each other, but I can guarantee you’ll save time by finding out right away rather than wasting time and money on a more elaborate date. And you’ll get valuable practice at the skill of looking people in the eye and having good conversations. The more comfortable it is for you, the more comfortable it’ll be for the next woman you meet. Because really, you need to be at least somewhat comfortable in your own skin and have minimal conversational skills for this to work.

So what happened to my friend who was thinking about planning more elaborate dates? He took my advice and simplified instead, and now he has a girlfriend. Last month, he took her to meet his family at Thanksgiving, and next month they’re going to Thailand together. Sounds like it’s getting serious.

 Stay sexy, my friends.

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