NYC Dating Tips: What a Relationship Expert Looks For on a First Date

Living in New York City, I will be the first to admit I’ve agreed to dates solely because I was blinded by a man’s height or his cute accent. Unfortunately, that has come back to bite me three dates later when I realize I’m at dinner sitting across the table from a man I have nothing in common with.

I may have had to learn the hard way one or two or maybe ten times, but it’s made me the well-seasoned dater I am. I know what I want in a man and I definitely know what I don’t want.

Everyone has their own things they look out for when it comes to dating, but here are just a few of mine to share with you.

Where did he choose the location?

The man is being evaluated before the date even starts. I live in New York City. Transportation and convenience are everything. Your date should be considerate where you live and choose a spot close to you. Immediate red flag if he chooses a place right next to his apartment. It means he’s either too lazy to look for new places outside of his neighborhood, or he’s hoping to take you back to his place after the date.

If he’s choosing a restaurant for the date, is he keeping in mind your preferences or dietary restrictions? It’s always nice to feel like someone is being conscious of your needs.

How did he dress?

So we made it to the actual date! I for one like a sharp dresser. I also think it shows a sign of respect. If I’m going to spend an hour doing hair and makeup, put on my best outfit and wear an uncomfortable pair of shoes all night, I expect some effort on my date’s end as well.

Is he asking me questions about myself?

A conversation should be like tennis. Back and forth, both people taking turns talking. It’s very easy to tell when someone begins to dominate the chat. It feels good when the man is trying to learn more about you because it shows he cares and is interested in getting to know you. It’s important to reciprocate the effort. Store everything he says as information to guide your decision on whether you want to see him again. 

Bonus: Don’t be afraid to throw in a couple of your non-negotiable, more serious questions. Maybe it’s about family or faith, we all have specific things we need to be on the same page about and that’s okay!

Is he a gentleman?

Yes, chivalry does exist, and I will not accept anything less and neither should you! The man should always pay on the first date, you don’t have to offer. He should be holding every door for you, walking on the street side of the sidewalk and offering you his jacket. Since the dates I go on tend to be within a ten minute walk from my apartment, if at the end of the date a man doesn’t offer to walk me home I won’t see him again. I like a well-mannered and polite man!

How do I feel when I’m with him?

Always, always, always listen to your gut, girls. I can tell something’s off if I feel like I can’t be myself around a person, or if I have to block off certain parts of my personality because I think they won’t like them. Of course there will be first date nerves in the beginning, but that should go away fairly quickly after meeting. Plus, don’t get awkwardness confused with discomfort or distress. Oftentimes for me it will manifest physically. Maybe it’s a pit in my stomach or just an all around uneasiness, but I know it’s my body sending me messages and that I need to listen to them. 

When dating intentionally, one of the best pieces of advice I can give is to write a list of all the qualities you want in your future partner. Remember, you can have it all. You don’t have to compromise. You are the full package, you deserve the full package. 

Most importantly when you go on a first date, try not to overthink too much. Dating should be fun! These are just things to keep in mind. Take it slow, be yourself and make sure he’s treating you like the prize that you are.

My name is Isabel and I’m a writer in New York City. I’m currently getting my MFA in Creative Writing Non-Fiction at the New School. I consider myself a relationship expert and I love imparting my wisdom through essays, blog posts and in person! I’m basically your go-to advice friend. Follow me here.