The State of Big City Dating Today

We’ve collected the best advice for all big city singles to benefit from…

Tawkify Matchmaker, Moni Oyedepo. Photo by Hey Saturday.

Tawkify Matchmaker, Moni Oyedepo. Photo by Hey Saturday.

Single in La La Land? You’re not the only one. Of the 51 largest U.S. metros, Los Angeles has the fourth highest percentage of singles (that is, 55.8%!). You might think ‘finding forever’ is more likely with so many eligible singles running about, but you’d be mistaken. Los Angeles is infamous amongst daters as a difficult city to find lasting love connection.

A matchable member in Los Angeles wrote-in and asked: “Is there some kind of secret LA dating language no one teaches outsiders? I’m newish to Los Angeles, and strangely, I’m not dating with the frequency (or quality) that I was in Chicago. I’d be most interested to hear back from local LA matchmakers.”

Your wish is our command, Allie! We’ve teamed up with Hey Saturday (the first and coolest dating photography agency) for a special Los Angeles dating article, featuring our local La La Land matchmakers.

We’ve collected the best advice for all big city singles to benefit from.

A big thank you to Tawkify member, Allie, for inspiring the topic, and also to the masterful photographers of Hey Saturday, who captured the spirit of our lovely LA matchmakers.

If you’d like a professional photographer to take your dating profile pictures, you’re in luck. Hey Saturday will be doing a complimentary photoshoot for one lucky Heartalytics reader in either NYC or Los Angeles! Enter to win, here. (Update: competition closed, a winner has been selected!)

Read more about this special photoshoot giveaway at the end of the article.

Professional Matchmaker, Amy De Souza.

Professional Matchmaker, Amy De Souza.

  1. I would argue that dating in LA is similar to dating in other major cities, like NYC. This rule applies everywhere: Don’t assume it’s exclusive until you’ve had that conversation (and until ya do, keep on dating!). You’ll be much less anxious about hearing from “the one,” if there are indeed, a few!

  2. Try and go on as many dates as you can (I aimed for 3/week when single in LA), it’s a number’s game.

  3. Don’t be so quick to write someone off. I have a lot of friends and clients tell me — if the guy doesn’t say something clever on a dating app (if he just says “hello” for example) they won’t even respond. That’s ridiculous! He doesn’t know you, he’s saying hello! Say hello back.

  4. Make sure to ask questions, it’s not all about you. But also remember to share, even if the other person isn’t asking you questions.

  5. Be on time. Nobody likes waiting around for their date, especially in a city where most people are working hard and free time is a luxury!

Professional Matchmaker, Moni Oyedepo.

Professional Matchmaker, Moni Oyedepo.

Moni Oyedepo:First dates are like a cocktail.”

While we all want to enjoy it and feel good by the end, there are sometimes key ingredients missing that result in dates falling short.

So, I recommend (especially in a city like LA) to go two parts RELAXED. First dates are exhilarating and stressful! While it’s OK to approach a first date with hope in “this could be the one,” a better perspective would be: “this could be a new best friend…” Yes. Babies and marriage and a lifelong travel buddy are all very nice, but at the end of the day, life partners become the ultimate best friend.

Ask yourself: would I even choose this person as a friend? Get that basic question answered before thinking of wedding veils on the Uber ride home.

One part OPEN-MINDEDNESS. First impressions are usually the worst, the most magnified, and not always accurate. That’s why I always encourage second dates.

In some cases, the first encounter was so terrible you’d be grateful to never share the same city block with that person ever again. But other times, perhaps you were both a bit nervous and maybe he/she didn’t handle that feeling as well as you did. If the thought of seeing him/her again doesn’t make you gag, and you realize that the minor irritants that previously clouded you from getting to know a great person weren’t that important — try again! You’ll be surprised by how things can improve once first date nerves are out of the way.

A hint of FLIRTY. I’m always amazed when people are gregarious with me on the phone, but then have stage fright on the actual date. Keep it sexy, people! I encourage my clients to do one flirty thing (if they’re feeling it!). Whether it’s a hearty laugh in response to a good joke, a light touch on the arm, or a sincere compliment is given, do what makes you feel most comfortable, interested and engaged.

“Free the flirt and get out of your own head!”

Just the tiniest dash of INTERVIEW. Yes, the whole point of dating is getting to know someone (and you should get a good sense of the person), but if you go into it with a list of questions and expectations, you’re going to walk away with answers, not a connection. You didn’t interview your best friend when you first met — this is no different! Vibes must be established before the checklist is pulled out. You’re looking for a long term Netflix buddy, not a new accountant. Keep this in mind.

A garnish of SELF AWARENESS. At the end of the day, dating is more about you than you might think. What am I talking about? While you’re assessing if the other person is a great fit, you also need to learn about the different ways you present yourself and if you’re always bringing your “A Game.”


  • Don’t tell that traumatic story about your family over appetizers anymore.

  • Or…skip the gym if you can’t guarantee time for a shower, smelling good is more important!

  • Stop looking at your phone during dates.

  • Work on that bad habit of fidgeting or biting your nails.

  • Get real, maybe it’s time to stop drinking twice as much as your date!

“So often, we nitpick the other person, but aren’t also being mindful of the things we do well (and not so well) on dates.”

Truly take stock of your behavior. What works and what doesn’t work for you? You’ll be surprised on how many notes you’ll walk away with on how much you’ve grown as a person and potential match after going through this process!

Professional Matchmaker, Gaby Aratow.

Professional Matchmaker, Gaby Aratow.

Gaby Aratow: “If you want a relationship, find solutions over excuses.”

A relationship is like a soup you cook together. Instead of looking for someone who brings the exact same ingredients, pick someone who brings ingredients that are also needed, but different — and then add the stuff you like on top! He/she doesn’t have to be a fine art enthusiast just as you are, to be a fabulous match! This universally applies.

In cities like LA, with SO many options, I think it’s important to study your own dating patterns. For example, if you have a history of chasing people who are hard-to-get, or emotionally unavailable, that likely means you need to conquer your own fears of intimacy. No one who is truly emotionally available can tolerate someone who isn’t for very long.

“This is a no-win game many singles play in big cities, so why play it?”

Sherrie Adams: “No matter the city, but especially in LA — abandon all expectations.”

If you let go of all preconceived notions and anticipated results, you accomplish two essential elements of dating success:

  1. You’ve taken the pressure off of yourself to perform.

  2. You’ve taken the pressure off of your date to perform.

When the pressure is off both people on the date, they can be their best and most natural selves! Both parties feel comfortable, unrehearsed, vulnerable, adventurous, open and fun.

I agree with Moni, you don’t need to have a checklist of questions and answers prepared. It’s better if you don’t! Throw all of that baggage away and instead focus on knowing your audience and having fun. Become an expert at tuning into the person you’re sitting across from.

Professional Matchmaker, Sherrie Adams.

Professional Matchmaker, Sherrie Adams.

Go with the flow. Your questions and conversations should be based on the person you’re with, not on a rigid list. Be present and listen to your date. Read between the lines, pick up on body language, be engaged. Every person you go out with is different and brings out a different side of you, but only if you’re open to it.

This is why dating is fun and revealing! If it’s a blind date or an online date, think of it as a going out with a friend you haven’t yet met. The less rehearsed you are and the more natural you are, the more attractive you’ll be — your energy will radiate over to your date and create a sense of ease. Dating is a dance, feel the beat and get into the groove.

competition officially closed.


No purchase is necessary to enter this competition! Check out the terms & conditions.

No purchase is necessary to enter this competition! Check out the terms & conditions.

Win a Big Adventure photo shoot with award-winning Hey Saturday, the UK and US’s premier dating profile photo specialists.  

Please note: Photoshoot will take place in either LA or NYC. Those who apply must live-in (and/or be willing to travel to) one of these locations to be considered.

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