Dating In New York Sucks, But Matchmaker Emily Holmes Hahn Has Some Tips

Love is a many splendored thing...

That is unless you're single in New York.

In that case, you're probably totally over the rom com dream, carrying around more bad date stories than you can count, suffering from a terminal case of Dating App Fatigue, questioning whether to get a cat, or just die a more noble death alone.

As the Founder of LastFirst, a personal matchmaking agency serving singles in New York, Los Angeles, Miami and more, Emily Holmes Hahn is in the business of dating - and she's the first to acknowledge that it is, well, real rough out there. Happily married herself, she's amassed a roster of clients all looking for "the one," and a growing folder of those on the wait list desperate for her magic marriage-making touch. 

Curious to hear her professional take on all things relationships and romance?

How did you get into the world of matchmaking?
Completely by fate! I was working in fashion in Paris when I received a LinkedIn message from a New York Matchmaking agency that was too intriguing to ignore. I interviewed, got the job, packed up and moved my entire life within a few weeks. I fell in love with this industry and ultimately decided to start my own firm about 10 years ago now.

How many marriages have you helped set up?
38 marriages and counting! We work with a small number of paying clients at one time, and only take on new business once a client is squared away in a happy relationship. So we’re super proud of this number and definitely keeping an eye on (or perhaps a little social media stalking 😊) our clients who are happily dating, waiting for that next engagement announcement.

What would you say to a single person frustrated with the New York dating pool?
Stop looking for love. Focus on yourself and what makes you happy, and the right partner will absolutely (eventually) appear. Or, if you’re in a hurry you could hire a matchmaker to focus on your love life while you focus on yourself!

Any tips for cutting a date short?
Ooh, great question and yes. This is basically the only dating scenario where I’d recommend a little white lie. You don’t owe them an analysis of why your personalities aren’t a match, or an explanation of why you’re not feeling chemistry at this stage. Use any excuse like having plans to meet a friend for dinner or needing to get to bed for a stressful workday tomorrow. Don’t make it outlandish or go into too much detail. I bet you they’ll know what you *really* mean, and if they do follow up to make another plan, you’re fine to just ignore it.

What's something people might not know about the matchmaking industry?
That we represent all kinds of singles. Sure, some clients want to get married and start families ASAP and that’s why they hire us. But even more are just genuinely seeking love, and whatever form that takes down the line. Most of our clients are still looking to be monogamous, but even that cultural norm has shifted substantially in recent years...

How did you meet your husband?
I’m equally embarrassed and happy to share that we met at a West Village bar! I totally pitched him on matchmaking at first, but realized by the end of the night that I wanted to keep this one for myself. We’ve been married 5 years now and actually named our dog, Wilfie, in honor of meeting at Wilfie & Nell.

Interborough relationships - are they doomed to fail?
Honestly, probably. More for lifestyle and values-based reasons than anything else, though.

Any thoughts on fancy first dates?
I don’t mind them at all, depending on the match of course. I think first dates have become too much of an afterthought— a 45-minute coffee wedged in between a workout and a dinner with friends. I’m old school and love making each first date an occasion. So if I am organizing a match where both people are foodies and like to dress up, I go all out with a reservation at a trendy spot like Nubeluz, Casa Cruz, or The Nines. I do draw the line at a white tablecloth, more fine dining establishments, unless the couple is much older. That’s an experience better saved for a birthday or special occasion date.

Splitting the bill?
That’s a no for the first several dates... if not for forever. It’s so unsexy to split the bill, so if you’re of equal financial means maybe alternate having one partner pay for dinner and the other can get the movie tickets, drinks, or whatever!

What are some red flags you feel like people often miss?
On a first date: showing up late without apologizing, being anything less than ultra-friendly to waitstaff and taxi drivers, and not sending a “thank you”/“nice meeting you” text to the person who proposed the date and paid. Later on: avoiding discussions about exes because they want to “focus on us,” not integrating you with their friend group, and controlling behavior of any sort (even if it seems like they’re just being confident and decisive!).

Where would you recommend going in New York to meet people?
Honestly, I think the average bar and restaurant scene has gotten really tough here. Everyone is swiping up a storm on the apps so nobody’s going out to socialize beyond their friend group. And there are so many weirdos at bars! I do like members’ clubs like The Ned or Zero Bond because at least you know that everyone there has gone through a sort of vetting process to join….so I feel there’s more normalcy to just approaching someone you’re attracted to, asking when they became a member, what’s good to order, etc. The Ned also hosts some interesting discussion groups and even singles events where it’s easy and encouraged to connect with others! Beyond that, think outside the box with unique workout classes, small comedy shows, and the #1 guaranteed-to-meet-somebody venue, dog parks!

What are your clients' most popular deal breakers?
Another fun question! Guys’ most common dealbreakers are cats, cigarettes and high maintenance vibes. Girls’ most common dealbreakers are height (if too short), hair (if there isn’t enough of it), and a lack of self confidence. And yet we stereotype men as the more superficial ones! I do think that men have a ton of looks-related dealbreakers as well, but there’s a much wider range of what ‘type’ of women men find attractive, than vice versa.

What's the most telling question you ask clients when getting to know them?
Hmmm. We’ve developed a 100-question questionnaire that guides us through each new client’s history and preferences. I love so many of our questions! My favorites include: “What is your most treasured memory?” “What are 5 objects you cannot live without?” and, “In one sentence only, what ended your last relationship?”

Is being too picky really a bad thing?
Sometimes. I have seen people completely self-sabotage their matchmaking experiences by finding something “wrong” with every date. It almost feels like an addictive game to them because they know that contractually, we’ll always be on their team and promptly send over another idea. I think there’s a real difference between “settling” and “compromising.” Settling is bad because it means you’re committing to someone who you’re not feeling strong chemistry with. Compromising, on the other hand, is a natural component of any successful relationship. Maybe you’re different religions, your friend groups have nothing in common, or you don’t share many hobbies — these are things that can be compromised on and worked out, in the name of love! These differences actually provide an opportunity for couples to come together and create their own unique identity.

As a matchmaker, what do you think of the dating apps?
Hate them! I think that our love lives are the one thing we cannot allow tech algorithms to take over.

How long might it take on average for you to help make a match?
It varies, anywhere from one week to two years! On average it takes about six months. A lot of the time, at the beginning of the process people think they want something a bit different from what they actually need in a marriage. So there is a bit of a learning curve for both the matchmakers and the Clients. By six months we’ve usually developed a clear vision of what someone’s dream match needs to look, think and act like, so we’re all on the same page.

Is there a particularly busy time of the year when it comes to people looking to settle down? 
Cuffing season is definitely our busiest time. Suddenly it becomes urgent for people to find a partner from September onwards, so we actually typically form a waitlist of prospective Clients right about now too, to make sure that our existing customers are getting all the love and attention they need!

What's your biggest piece of advice to someone looking for love?
Love yourself first and the rest will fall into place. The only relationship that literally lasts forever is the one you have with yourself, so you must nurture this relationship above everything else. The right people will notice a man or woman who has done this work, and will want to be around them.

[Photo via @rosewoodthecarlyle]