Love on 27th Street: How To Know After The First Date

A Note from the Director: Love on 27th Street is a spin-off of our recent column “Sex on 27th Street”. A change in writers of the column has inspired us to expand it to more than just sex and into love and relationships between lovers, family, friends, etc. Alice Sungurov is our new column writer for Love of 27th Street. Alice will be writing to you on Saturday mornings. 

Alice Sungurov | Writer of Love on 27th Street, Blush Podcast Producer and co-host

What is the thing you need to happen for a date to be considered a success? If you are the one being invited out, is it the pick of the venue? Whether your date pays for you? How do they dress? Is there a kiss at the end? Sex? Indeed everyone has that “thing” that seals the deal on whether a date can be considered good or not.


For me, in some sense, it’s all the things listed above in varying degrees. However, whenever I leave a date, the first thing I ask myself are these three questions.


  1. Did he ask me questions?
  2. Was he listening to what I had to say? Did he engage with my responses?
  3. Did he compliment me?


I know these seem simple, but if you are looking for more than just a one-time hookup, I PROMISE these are the questions you need to be asking yourself. 


So, let’s break this shit down. 


Question One: Did he ask me questions?


The most important aspect of a date is conversation. Without that, there is no date, just two people awkwardly sitting staring at the ceiling. 


When someone asks questions, it invites an exchange; thus a rapport can be built. Now, when I say questions, it can’t just be “What do you do for work?” “Where did you go to school?” There needs to be subquestions. “What made you go into that field?” “What’s been your favorite part?” “What was the go-to bar in your college town?” 


You want to feel like someone’s interested in your life– why you are the way you are, what led you there. The same goes for you with them.


Some of my most memorable dates happen when I remember a forgotten memory through the series of questions and exchanges. One time, I was telling this guy about a trip I took, and he then asked me what the worst thing I ate there was, and like Raven-Symoné, I was teleported back to a wild drunken night at a McDonald’s a three a.m. eating cookies and cream milkshake dipped french fries with my two best friends in a random-ass city in Europe. 


Question Two: Was he listening to what I had to say? 


This is piggybacking from my previous point, but it’s important enough to deserve a little elaboration. 


Have you ever been in a conversation with someone but behind their nods and occasionally “oh” there’s nothing– like that person is an automated machine pretending to be listening. People who do this think it’s not noticeable, but what makes it any different than someone simply ignoring you and looking down on their phone?


This may sound repetitive, but I swear taking a moment to answer this question makes a difference between going on any further dates or just ending it right there. 


Question Three: Did he compliment me?


Okay, now I’m a confident gal, and my self-worth doesn’t come from compliments from others. However, my old-fashioned Russian mother drilled this idea into my head, “He should compliment you.” 


She would then justify it by saying, “You spent hours looking good– doing your makeup, choosing the outfit, etc– so he better acknowledge your beauty.” Imagine this with a thick accent, it makes the wisdom seem wiser. “Also, compliment him. He needs to feel like he’s cool when he’s with you,” she would add.


In conclusion, is this the full-proof method to finding Mr. Right? No. All I’ll say is that this works for me to weed out the yes’ and nos.


Till next week gorgeous people,