It’s getting cold outside here in NYC, so I figure tonight I’ll bundle up on the couch, turn up the heat, and stay in for a movie, some Italian takeout, and a nice bottle of red.

While I’m thinking about it, bars are the farthest thing from my mind right now.  But it’s still Friday, so let’s talk about something relevant: going on a date.  Specifically, Friday night first dates, which I know a lot of guys tend to overthink.  So I’ll break it down and share an email I got from a client this week:

Hey Shogo,

Just wondering is there a polite way of asking a lady to pay for herself for an expensive outing?

I’m thinking about inviting this girl to an expensive concert, which costs $400.  I wouldn’t mind paying if she’s my girlfriend.  But, I barely know her and don’t know if it’s going to work out.  I know she likes music.  She’s in real estate, and I’m pretty sure she makes more $$$ than I do.  So, I wondering if I should ask her to pay for herself, forget about this whole thing and invite her to something else, or just take the risk and pay for her ticket and see what happens.  What do you think?

*I know they talk about ROI in dating, and this is an example.

Thanks in advance Shogo,

Jerry, New York City

Expensive Dates... Get it?

Jerry, good question.  Actually it’s two questions: 1) How much is ok to spend on a first date?  2) Can she pay her own way?

This is an expensive excursion we’re talking about.  Even if you’re banking some major green, a $400 event is just not date material.  It doesn’t matter if you can afford it or not.  Because even if you can, unless you want to be seen as a walking talking ATM or just another a guy who’s desperately trying to impress her, it’s a terrible idea to drop this much cash on a first date.

Ask yourself: do you really want to go to this concert?  Would you go to this concert if you went by yourself or with a buddy?  If the answer is no, then scrap the idea and do something else.  Go on dates where the activity is something that you actually personally want to do (or you know that she’s really going to enjoy—which in turn makes you want to do it too).  Don’t take a woman out for a first date that you would not want to do anyways.  You plan a date based on something that you want to do for fun, and as an added bonus, you have a great woman to share your time with.

So assuming this is a concert you really want to go to, if you’re going with her as friends, invite her along.  Just as you would invite a friend, tell her, “Hey, Sting (or whoever the hell costs $400 these days) is playing in concert next weekend, I really want to go and since you’re such a fan, I thought you’d be interested in going.  Tickets aren’t cheap though.”  Now you’ve implied that she’s got to pay if she wants to come.  Keep in mind that this is not a date.  This is you inviting her as a friend.  (It doesn’t mean you can’t date her later on down the road, but for now she is not your date to this event, so don’t treat it like one.)

But if you want to ask her out on a date, then ask her out.  And that means you pay.  My rule of thumb for guys is to ALWAYS PAY on the first dates.  Depending on your relationship, you can split (or let her pick up a check) later on down the road when you’re seeing each other on a regular basis.  But for now, you invited her, you pay, and you lead her on that date.

So that means that every date that you invite her on should be within your financial means to pay for both of you.  It can be dinner if you want (make sure it’s a place you actually enjoy going to; even better, a place you’ve been to many times before), it can be drinks, or just a simple coffee on the weekend or a stroll through the park or the holiday market—which costs nothing.

A date should never have to be “risky.”  A date should always be fun no matter what the outcome.  You should never feel like kicking yourself for having spent money on taking her out if the date turns out to be a flop.

How much would you pay for one night?

When you are spending money on things to go out and try to attract women, that’s when you think about your ROI, your return on investment.  But forget about the ROI when it comes down to the date itself, because on the date you are not spending money to try to attract the woman you’re going out with.  Your return on the investment is how much fun you had on the date itself, not what may or may not happen with her sexually after the date.  The money you spend is just window dressing for your leisure time—it does not buy anything from her, so do not expect anything.  If something happens, great.  But make sure it has nothing to do with the money you spent.  That’s just you and her being attracted to each other, and that’s not something money can buy.

So she doesn’t like you at the end of the date, or you don’t have chemistry, or whatever—you want to walk away from every first date with the attitude that you had a good time no matter what.  If there was no attraction, well then at least you learned something about yourself.  Or you practiced your skills communicating with a woman.  Or you learned something about how women work and it will make you better for next time.  Or you can walk away as friends and you’ve added a new person to your social network.

There is always an upside to every encounter with a new woman.  And that’s what you focus on.  Maybe the date works out, and that’s great.  But even if it doesn’t, don’t chalk that up as a lost investment.  Think about how you grew.  What you learned about your skills connecting with this woman, what you learned about women in general, and what you learned so you can improve the next time.

No date should ever have to be financially risky.  Eliminate that “risk” right out of the equation by asking yourself, “How much would I feel comfortable spending just to hang out and get to know this woman even if things don’t work out?”  And you will have your answer.

I’m about to give you six easy things you can (and should) do to impress a woman on a date. As you will see, none of these six things involve picking out the right food or the right restaurant.

1.What Do You Know About Her?: So what do you know about this woman you want to impress? What are her likes and dislikes? In order to plan a great date, it has to be something that really interests her. A lot of guys do the standard “take her out to dinner” thing and just hope for the best. In reality, though, that’s just not the right way to do it. You need to think outside the dinner box, and think about something that will show her you thought about her when you planned this date. Picking something that relates to something she likes or in which she’s interested goes a long way.

2.Have A Plan: There’s nothing that turns a woman off more than when you call her and ask her what she wants to do on a date. It’s called listening. It’s about knowing what she likes. If you like her, you will do things that resonate with her, and you will know what (at least some) of those things are because you’ve been listening to what she’s had to say when you’ve talked to her. Also, women like strong, confident men. Women like men who have a plan.

3.Activity Dates Are Great: When you plan your date, do something where you can challenge each other and have fun. Go bowling. Play miniature golf. Go to one of those pottery places where you can paint a mug. Take your dogs for a walk. Go get some ice cream. Instead of just having dinner, take a walk around a lake. Do something that’s casual, fun and no pressure. The problem with going to dinner on a date is that is can feel very high pressure. You are sitting across from each other with nothing to do but watch each other chew and resume swap. Do something more fun than that, and the more child-like the activity the better. Plus activity dates give you lots of easy conversation topics.

4.Have No Expectations: Even though you are so excited to be out with this woman, you really don’t know who she is yet so why have expectations? When you have expectations, you have pressure to make things work. By remaining present on the date and by not thinking ahead to other dates, you’ll actually have more fun (which will give the date a much better chance of being successful). The reason why so many dates go south is because you’re thinking ahead during the date. In reality, though, all a woman wants is the real you. She wants you being present and being engaged in the moment with her. She wants the real you, not the “playing it safe” version of you.

5.Don’t Worry About The Goodnight Kiss: If you both have a good time on a date, then don’t worry about the goodnight kiss. So many times, guys feel like they have to “seal it with a kiss.” So many times, guys will start thinking about the goodnight kiss the entire last part of the date. It’s like it’s the 4th quarter of a football game and they’re planning their comeback, when what they should be doing is just enjoying the play-by-play. When you walk her to her car, just give her a hug or a little kiss on the lips. Don’t worry about the full-blown makeout session. Women love foreplay, and they love to be left wondering about that passionate kiss they will have with you.

6.Follow Up With A Second Date: If you had a good time and she had a good time, then why leave her in suspended animation? Ask her out for a second at the end of the first date, and ask her to do something you both talked about enjoying on the first date. That way, when she goes home and does the play-by-play with her friends, she’s going to say that you’re one of the few guys who didn’t leave her wondering what she did right or wrong on that first date. You will stand out among all the “other guys” she’s met.

As a man, you want to be a leader. You need to remember that women love romantic comedies. They are always looking for that serendipitous moment where a man just knows things about her and takes her to her favorite coffee shop without even having to ask her which one that is. You want to be the leader, not the follower. You want to lead her on a romantic journey. So taking her to a restaurant and watching each other chew just isn’t going to cut it. It’s time to get creative.