In New York, everyone is busy. It seems like everybody has a day job, a night gig or a side hustle and if they don’t, they’re desperately looking for one. With the constant need to chase money, opportunities, or inspiration, it can be hard to find the time to date or to get to know a person at all. As a firm believer in making time for people and things I find important, this year I’ve pushed myself to make the first move also known in 2016 as “shoot my shot.”

While being assertive in the pursuit romantic relationships is new for me, I’ve noticed how weary many men are to being approached first. Most times, a woman’s actions are misinterpreted. A few consistent calls or texts can be read as a woman “wanting more” when actuality, we’re  just communicating.

Some men are taken aback by a woman making the first move and see it as us “not staying in our place” — stay away from those types. While others take the assertiveness as a sign to completely fall back when it comes to scheduling dates or communicating because we’ve been making the first move all along.

I spoke to boss woman and Jane of all trades Chelsea Harris about why she’s fallen back from shooting her shot, the importance of planning, and more for the latest installment of Dating in NYC.

Read her thoughts below:



What expectations do you have going into a first date?
First dates are nerve-wracking. More than anything, I just expect authentic conversation and for him to be a gentleman.
What about a first date makes it nerve-wracking to you?
The anticipation of what’s to come. I’m learning not to think about it too much and just enjoy the moments. You’ll drive yourself crazy with questions like “Is this outfit cute enough?” “Will he be another disappointing first date?” or “Will he end up being bae?” I’m settling myself in the idea that whatever’s for me will not miss me.

Describe your best dating experience or ideal date:
First of all, make a plan! Lately, I’ve been experiencing men that hit you with a “Wyd?” at 6PM and want to know if you’re free to grab dinner at 8PM. While that may work sometimes, I appreciate it way more when a man is considerate of time.
I have an art background, so art galleries or museums and dinner afterwards is always a great time. Whether it’s art, music, or etc., I find that it’s easier for people—myself included— to let their walls down when they’re experiencing something new.

Describe your worst date:
I went on with a guy I met off Instagram, he wanted to grab dinner. I was excited because he asked for my number and didn’t waste a lot of time setting up a date.

Long story short, I arrived dressed-up—nothing crazy, but you know.. the works. He arrived in a hoody, baggy jeans and sneakers with a North Face bookbag carrying a Snapple. Later, as I was looking at the menu, he expressed that he really wasn’t even hungry. He ordered a Corona and said he didn’t want to order a real drink because he already had liquor on him. He motioned towards the “Snapple Iced Tea” and I realized that it was actually Hennessy he had brought with him.

I’ve done my share of putting Henny in a Snapple bottle en route to a Summer BBQ, but we were two adults on a first date. Needless to say, I was polite but opted to not speak to him after the date because the overall vibe of the date felt a bit immature.

Has your dating experience made you more or less inclined to keep trying?
This varies on the day, but I’m open-minded.

What keeps you open minded when it comes to dating?
I’m just naturally a hopeless romantic. I believe in people. I also know there’s someone out there who feels the exact same way about today’s dating climate as I do. All I can do is continue to be the best me I can be, and the Universe will bless me— and that’s with anything, not just dating!

What’s your take on women “shooting their shot”?
I’m naturally an assertive person and I also have to be assertive in my line of work. So romantically, I prefer that the man pursue and lead. I find that any time I’ve “shot my shot” with a man he’s been lazy in his efforts because he’s seeing it as “Well, she hit me up.”

How do you go about shooting your shot?
I’ve done it before. About two years ago, I think we exchanged Instagram handles—weird world we live in now—and then I DMed him first. I made a dorky joke about grabbing apple juice or something—he didn’t drink alcohol.
Now? I have ways to let a guy know I’m interested, but I’m not really into shooting my shot. I believe in making a man feel special, but in terms of the initial pursuit? I think it should be up to him to take that first step.
If you’ve dated men not from NY, what differences did you see between them and NY men?
I find that there isn’t as much ego involved when dating a man that isn’t from New York. I love that NYC pride, the grind, and grittiness. But, I think our men forget that they need to soften up a little in the presence of a woman. I don’t need you to puff out your chest like you’re more than what you are.

Let your guard down, be sweet and chivalrous.

Does your profession affect the type of men you date?

100%! I find that many men claim they want a “boss chick,” but I’m not sure if that’s true. A boss chick isn’t sitting by the phone waiting for you to hit her up. She’s got shit to do and her time is valuable. It’s not just men that should be respected in this way. I’m always hustling, chasing inspiration, or networking opportunities. So, it’s important I date someone that is on my level.

How do you balance work life and dating?
The key is to make yourself a priority while still keeping things exciting in your love life. It’s also fun to work around obstacles. Like if he or I are out of town for work, scheduling (nasty) Facetime dates.
Do you think that social media has affected the way we date now?
1000% and I hate it, but it also feels like an unavoidable circumstance. It has really distorted people’s perception of closeness and successful communication.

If there was one thing you could change about the dating scene, what would it be and why?
Honestly, I’m tired of this weird pre-dating “talking” stage. Basically, some men are prolonging the first date and are using texting as the “getting to know you” stage. I’ve heard a lot of girls are experiencing this. Part of my theory is that social media has increased people’s weariness of each other and many are afraid to be “deceived”. Personally, I love eye contact and I think body language is important. In person, I can tell right away if I’m going to hit it off with someone; whereas via text it’s harder to tell.


One of those "I like MF DOOM" type girls trying to figure out life in her 20's.