New York City dating tips

How many dates a week is a good combo of getting out there but not being sad?

I think 2-3 dates a week is a good number. You don’t want to be going out every night of the week, and trust me even going out on 2 dates a week is a lot of work logistically. (especially if they are different women, then you have to work your schedule to fit each in on different nights) You also want to leave some nights for hobbies so that when women ask you what you do for fun your answer isn’t “dating women”.

How do I manage the second date and thirds when I have all these people I really like the sound of and haven’t met yet. Seems rude to put people off before I’ve had a chance to see more people?

You’ll know when you would want second or third dates. At first when I was casually dating I would go on second or third dates often until I felt there was absolutely no chemistry or if the woman felt the same. After awhile I really became attuned to what I was seeking in a woman physically and intellectually and now I can say “no” before ever going on a date. Over time you will naturally become more selective.

Is a drink OK for a first date or do people expect a meal?

In New York drinks are fine for a first date. They are more casual and gives you the chance to get to know one another. Dinners are more formal and send a more serious message. You can do dinners as well but just know that you are expected to pick up the tab. This can get expensive if you’re out on 2-3 dates a week.

Are weekends out of bounds for first dates, they would be in the UK.

Weekends are not out of bounds for a first date, but they are harder to book. Here in New York, Friday night is considered “part of the weekend”. Saturday’s are almost always the hardest night because that’s the night when everyone wants to go out with their friends. Sundays are a sneaky great day to have a date. An early dinner is nice since the restaurants aren’t packed, and the relaxed vibe of Sunday is nice for getting to know people.

Is a kiss on the cheek a good first greet?

A hug and a kiss on the cheek is perfectly fine.

If there is good chemistry after a 2 hours is it a good idea to go in for a kiss or is that a bit much?

You will know when she’s ready to be kissed. As a general rule I’ve never kissed a woman before I’ve held her hands. Sometimes they reach out to me, sometimes I reach out to them. At the end of the night you just get the feeling that they want to be kissed. Look at them in the eyes. If things get quiet and she doesn’t look away, it means she wants to be kissed.