Guys stress way too much about first dates. A first date should be simple. It's just a chance to see if you are compatible and find each other interesting. It should be about the two of you, not about the activity.

Keep it short

A first date shouldn't be something that takes a lot of time. For instance, going to a baseball game could be a great date, but it's a bad first date. It leaves both parties feeling trapped together for 3+ hours, and doesn't provide any flexibility. What if you have terrible chemistry?

I made the mistake once of having a first date at a board game bar. It seemed like a great idea-- it was cold outside, the bar had hot apple cider with whiskey in it, and I figured board games would be a great way to get us both to loosen up and have fun.

As it turned out, I had an incredibly hard time making conversation with the girl, and I realized by the time I had played my first Scrabble letter that it was going to be a very long date. Aside from being challenging to talk to, the girl spent at least 5 minutes staring at her tiles each turn, deciding what to play. It was hard for me to come up with good words when I could only think A-G-O-N-Y and E-X-C-R-U-C-I-A-T-I-N-G.

Had I just opted to get a drink or a coffee for our first date, I could have gulped down a beer and we could have said our goodbyes in 40 minutes. Instead, it was a two hour date that I imagine left neither of us happy (I lost the Scrabble game, too).

Don't get me wrong-- I've had plenty of first dates that ended up lasting hours, but they should do this naturally. It's an awesome feeling when the coffee shop you're talking in is closing down and you both decide to head to bar to continue the date.

Keep it simple

Choose an easy, relaxed activity that doesn't have to take more than half an hour. A drink, a coffee, a ice cream and a walk in the park, whatever.

However, just because a first date should be simple doesn't mean it can't be interesting. Use the date as an opportunity to go somewhere new that you've been wanting to try. There are unique bars, coffee shops and hole-in-the-wall restaurants in every city; check them out.

I've found that in general, girls love places that are "cozy." If you're stumped as to where you should take a girl on a first date, enter this query into Google:

Yelp: cozy bar Boston

If you figured out that you should replace "Boston" with your hometown, congratulations. You must be quite the catch. This query will give you some spots that real live people think are cozy, and you can narrow down from there.

Choosing a cool, unique spot will give you something to talk about on the date, it will make you seem more interesting in the eyes of the girl, and you'll naturally have more fun if you're discovering a new place together.

The other option I recommend for a first date is to bring her to a local spot you know really well. If you have a park, a bar or burger joint that you love and are proud of (the kind you take your friends when they come from out of town), it can be great to take her there. If you're excited about showing her the spot, it will shine through when you talk, and she'll respond to your enthusiasm. It will also make her feel closer to you to see a part of your world.

Where exactly you take her can depend on what you're looking for. If you're looking for something more serious, I'd suggest coffee or lunch-- it implies that you're willing to invest time to get to know her. If you're looking for something more casual, a drink in the evening is a better bet.

The first 5 minutes

The first 5 minutes of the date are going to be a tad awkward. That's okay. You're both nervous, it's to be expected. Here are some things you can do to make the start of the date smoother:

  • You should arrive 5 minutes early, and have something to do. * If you're at a bar, order a drink; you can look at your phone, whatever. Sit near the door.
  • When she arrives, stand up, smile at her and wave. I've never had a problem recognizing a date from a dating app, you'll be able to tell by the way she enters the room.
  • Give her a brief hug hello. I've found this to be the best greeting, and if you decide to do it beforehand and go for it with confidence it will save you both from trying to decide whether the person wants to shake, hug or wave uncomfortably.
  • Have a sense of humor about it. Act as if the awkwardness is an inside joke between the two of you. You aren't Daniel Craig (unless you are, then please will you mentor me?), you don't have to be James Bond. Acknowledging the awkwardness will ease both of your nerves.
  • Ask her what she's been up to that day. This is an open-ended question and you can continue the conversation based on how she responds. If she says she was working, you can ask, "oh, what made you get into your line of work?" If she was watching TV, "What sort of shows do you like? Are you a movie person?"

Above all else, don't take the first few minutes too seriously. The more relaxed you seem, the more relaxed she'll be, and the quicker you'll be able to establish a connection.

Make it your mission to find out about her

During the date, think of yourself as a sociologist who is trying to learn about this particular human being. Explore her world, figure out what she likes, what she hates, how she got to this point in life. Let her talk. One of the best things I've learned is to ask open-ended questions. This means avoiding yes-or-no questions.

Let's say the girl tells you she worked at a camp as a counselor throughout college. Instead of asking her, "did you like it?" you should ask, "What was that like?"

The first invites a yes-or-no response, the second invites her to talk in more detail about her experience. She'll naturally talk about the things she feels most strongly about, and you can continue to ask her about it from there.

Avoid asking "why" questions

This can sound accusatory. Instead of "why don't you eat meat?" ask "what was it that caused to you become a vegetarian?" It is a small thing, but it makes conversations flow better and will make the girl feel more comfortable.

Keep your posture open

A huge part of making someone comfortable in a conversation is your body language. A good rule of thumb is to always have your body "open." This means don't cover your torso with your arms-- doing this conveys insecurity. It's a very primal instinct to cover up your most vulnerable parts when you feel nervous or scared. Learning to resist this urge will make you a better conversationalist. You can learn a lot about this by watching Oprah Winfrey interview someone. Her whole job is making people comfortable enough to open up to her.

Who pays?

This may vary based on your financial situation, but I have always gone into a first date expecting to pay. This shouldn't be a huge burden, since you're not going anywhere fancy. Oftentimes, the girl will say, "Oh, we can split it," at which point I generally say "No, it's my pleasure." After that, if she insists on splitting it, I let her pay her half.

It shouldn't be something you worry much about. Girls I've asked generally say they don't expect their date to pay, but they appreciate him offering.

After the date

Offer to walk her to her car or wait for an Uber with her. If you had fun, tell her you had fun, and that you'd like to see her again. You'll probably get nervous wondering whether or not you should kiss her. My thinking on this is as follows: On the first date, don't kiss her unless you're sure that you should. On the second date, kiss her unless you're sure you shouldn't.

My reasoning is that I've been met lots of girls who simply don't like kissing on a first date, no matter how they felt about a guy. One of them was when I was brand new to dating apps, and I kissed her anyway. It was really uncomfortable and clearly not the right time. Thankfully, we went out again and could laugh about it, and eventually ended up having much better kisses.

Another time, I went on what I felt was a really good first date, and actually asked the girl how she felt about kissing on the first date. She said she wasn't into it, and I left feeling deflated. She texted me the next day to come over and hang out at her apartment. I was confused, but went over, and we ended up making out. She said she appreciated that I asked, but just didn't like kissing on the first date.

Because of all this, I don't think it's worth trying to kiss a girl on the first date unless you're sure of it. If the date was really good and you liked each other, she'll go out with you again and you can kiss her then-- plus, it she'll leave the date wanting more.

For anyone who's interested, I write more about this stuff here

Good luck out there! Would love to hear any other strategies people have found that work well.