Based on data from 20,000 dates, professional matchmaker reveals how to create the perfect first date
Let’s talk about the first date.
You just planned your very first rendezvous with someone new. You don’t know too many details — first name, job, hobbies, maybe a few photos — but you have a feeling it’s gonna be good. Then you notice a “fluttery” feeling in your stomach and catch yourself repeating scenarios in your head. Yup, those are called nerves. Most people experience a type of low-grade anxiety before dates. You know the type just lurking beneath the surface—it’s not sharp enough to poke through but it’s not so subtle you can ignore it. Yeah, that kind.
I feel like the reason we experience nerves before our dates is because we fear the unknown. When we can’t predict an outcome with certainty, it becomes a risk. For example, when we can’t predict with certainty that our date will like us, it becomes a risk to our ego. But fears are not based on reality. Fear of the unknown is based on a pile of self-limiting beliefs based on what we think may happen. These self-limiting beliefs leak out in different ways; we fear our dates wont find us interesting, attractive, funny, or whatever insecurity we may have. As Ambiance Matchmaking’s Founder Leslie Wardman always says, “Insecurity is the root of all evil when it comes to relationships, and especially dating.” However, we can dissolve our insecurities and fears so that we can stop worrying and start connecting with our dates on a whole new level.
“I learned that courage was not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear.”Nelson Mandela
In order to conquer our fear of the unknown, we don’t just ignore it, we embrace it. We embrace the unknown because it brings change; and that’s a good thing. The one thing that is a constant in our dating lives is change; we’re constantly changing and evolving by meeting new people, hearing their ideas and stories, and trying to make sense of why we did or didn’t click with someone; and that’s a beautiful thing. So, let’s stop trying to predict the outcome of our dates, stop worrying about what people think of us, and embrace change. At that point, we can start focusing on connecting with the person sitting in front of us. And that’s exactly what we’re talking about today — connecting with our dates on a whole new level.
I’m doing it with the help of my colleague Leslie Wardman. Our company Ambiance Matchmaking has been matchmaking for over two decades, with as many as 20 matches going out every week. That means we’ve orchestrated around 20,000 dates in total. And, after each date we receive feedback from every client. As you can imagine, we have a lot of information about what people find attractive and not so attractive on a first date. Today we’re sharing those details with you. We’re starting with the top three reasons a date will find us attractive, and how we can implement these tips into our own dating lives.
Let’s call Leslie Wardman and see what she says…
What are the top three reasons someone will like their date?
Leslie: I believe a smile is an incredible way to express the fact that you’re comfortable in your skin, easy to be around, and happy with what you see (your date). I can’t think of anything that’s more powerful and positive as a first impression.
Me: Whether we realize it or not, we are portraying certain qualities through non-verbal action all of the time. 90 percent of communication is non-verbal; body posture, gestures and tone of voice are all signals that our dates pick up quickly and naturally. We might not be aware of these factors; but it’s a good thing to be aware of.
Leslie: Let’s not forget eye contact. When someone is smiling when you walk up to the table, or vice versa, it’s a good indicator that there’s going to be little or no awkwardness, and conversation is going to flow. Go with a smile.
Leslie: Vibe — which means having the same energy level — and being comfortable in your own skin — which comes by getting to know yourself. Good eye contact also indicates that you have a good flow of energy. If someone doesn’t have the ability to have eye contact, it shows they’re uncomfortable and don’t have the ability to be honest, and those are big red flags.
So, just being comfortable and being able to hear somebody share a story about their life and vice versa; maybe your story bounces off of theirs with laughs in between. Those are such good signs of a good date.
Me: Energy is everything. I’m reading a book by Joe Dispenza called Becoming Supernatural and he says, “Our emotions are energy in motion.” When someone experiencing a strong emotion walks into a room, their energy is often very palpable. So, that’s why it’s so important to get into a great frame of mind before our date; because our emotions are literally radiating off of us, and when we put off better energy, we get a more positive response from our date in return. And getting into a great frame of mind before a date could look like listening to a great podcast, reading a great book, calling a best friend, going for a run, you know, doing something you enjoy doing so that you can get into a great frame of mind before your date.
Leslie: Storytelling in my opinion is a lost art. I can’t tell you enough how wonderful it is to spend an evening with an interesting person with a nice flow and exchange of stories. There’s hardly anything better in this life. So, yes, definitely an exchange of stories with an interesting person. Even just saying that, I’m picturing a beautiful outdoor cafe, with stars, a glass of wine. I mean, that’s a good life — that’s definitely good times.
Me: Storytelling is such a great way to display your personality and give insight into your life. And it eliminates the somewhat boring and sometimes interrogative style of asking a slew of questions. But as you said, storytelling is an art and it involves having life experience and being a somewhat interesting person
Leslie: It’s important to be interesting. You don’t want to be sitting there on a date like a bump on a log and not have anything to talk about. You better get some experience in this life or you're missing out.
Me: I agree. Mark Manson and Tim Ferriss both talk a lot about self-diversification as a means to leading an interesting life. Mark Manson that said, ”When you have money, it’s always smart to diversify your investments. That way if one of them goes south, you don’t lose everything. It’s also smart to diversify your identity, to invest your self-esteem and what you care about into a variety of different areas — business, social life, relationships, philanthropy, athletics — so that when one goes south, you’re not completely screwed over and emotionally wrecked.” I love that because so many of us want to focus and specialize in only one field when in reality, it’s a much more enriched and beautiful life if we can invest in a variety of different areas, and it makes us a more interesting person, and it’s going to allow us to have so much more to talk about on our dates.
What are the top 3 reasons someone will not like their date?
Talking too much
Leslie: If you get to the table — besides the fact that your chair may have not have been pulled out, and you didn’t get greeted with a smile — and they start rambling on and on about themself — that is a huge buzzkill. Especially if all they talk about is work. I heard a story recently that on a Zoom date, the guy kept taking a work call during the date. He thought it was a positive reflection on himself, like ‘Hey I’m a banker, I have all of these important things going on,’ but nothing could be further from the truth. Just don’t sit down and start talking too much. Non-stop talk about work is not pleasant because it signals to your date that you don’t have a good work-life balance. Yes, work is important but have stuff going on outside of work because it doesn’t indicate who you in the big picture.
Not being present
Leslie: So many people are not present; things just fly over their heads. It’s a practice. Ask yourself, “Am I being present around this person, or do I have too much bouncing around my mind?” We really need to understand what being present means. Being present means not being preoccupied; not having a million things going on inside your head about that day, or yesterday, or tomorrow, or anything except for that moment; and being able to invest in that time that you’re with that person. If you’re not in the present moment, it’s just going to be a waste of time. This applies to everyday of your life. Also, practice listening — really listening — don’t look around the room, or at your watch or phone, or anything. Give the courtesy and respect, even if you’re not falling in love.
Me: That’s a good point. Even if you know you’re not going to fall in love with this person, you can always learn something new from someone. So use it as an opportunity to practice being present and learn something new about the person even if you know it’s not going to turn into a romantic connection.
Leslie: Worst case scenario, you find yourself in an awkward situation and you’re tempted to default to your dark side and not be polite; don’t. Be courteous, have manners, be kind, nice, considerate. Just do it out of being a nice person. Be nice.
Inconsiderate (no manners)
Leslie: Don’t be inconsiderate when you’re on a date. When you’re match arrives, don’t be on your phone (don’t be texting, don’t be talking, don’t be scrolling). Have your phone away and have it off. When your match arrives, (if you’re the guy) be a gentleman and pull out her chair. It’s a nice reflection of you being a gentleman. As you’re sitting and exchanging stories, don’t look around the room. Be nice and considerate to the wait staff, without being too nice; don’t flirt or compliment the waitress on her dress or anything like that. That is inconsiderate to your date. Pick up the check (again, if you’re the guy) at least on the first date. Normally, you wont be anywhere too expensive that will break the bank. It’s a really nice old-school chivalrous way to end a date. My all-time biggest pet peeve of inconsideration is when a guy doesn’t walk a girl to her car, hailing her a cab, or waiting until her Uber arrives. It’s not that difficult to take a few minutes to make sure everything is all good.
Me: I had a client ask me about this just the other day. We were talking about the liberal feminist movement, and how it’s influencing dating, and making men second-guess whether they should do things that are normally seen as chivalrous. Our client is someone that likes to open up doors and pay for dinners and all that, and he was saying how some of his dates have hated that. So I think some men are struggling with striking the right balance of being chivalrous and respecting a women’s independence and empowerment. I understand both perspectives, but to me, in its most simple form, being chivalrous is really just doing something nice for your date, which shows that you’re interested in her and you’re confident enough to show it, and that is a huge compliment. You know, a man isn’t opening your door or paying for your dinner because he thinks you can’t; it’s simply a nice gesture.
Leslie: Yeah, it definitely is. We’re at such an awkward phase when it comes to that because so many women are wanting to liberate themselves on many levels. It’s huge, but I’ll tell you what the big dilemma is; who’s going to pickup the check? It’s so awkward. Here’s what will bother a guy— when a woman just sits back and assumes he’s going to pick it up like its her birthright to get fed by this person. Typically, in the back of a guy’s mind, he’ll want to pickup the check and will 90% of the time, but its not well-received if the woman acts like she expects it. It’s nice if she indicates appreciation, like saying thank you so much, but there’s a flip side to that coin because some woman don’t like to ooze with appreciation. We could talk about all of the little nuances of this for over an hour. Again, this should just flow naturally. Let’s say the waiter brings the check and it’s sitting in the middle of the table — awkward moment — and the waiter normally puts it down in front of the guy 90% of the time anyway. If I were the girl, I would offer to pay half. The guy can say no. If he accepts, it might be a huge turn-off for some women. Everybody is different; just be aware and don’t assume anything because it’s 2020 and things have changed quite a bit.
Me: I agree. I would always offer to pay because I never wanted to assume, but even though it is 2020, I’m a little bit old fashioned when it comes to that and I really like the gesture of a guy picking up the check at least on the first date. So, if he wanted to pickup the check, I always showed my appreciation and say thank you so much; but if he accepted my invitation to pay half, that was a big no-go for me.
Leslie: It’s no reflection on anybody’s character or lack thereof. It’s something that we’ve been raised with, and our parents have been raised with, and their parents have been raised with. It’s just indoctrinated in us, whether that’s good or bad, its neither or. It’s just a reflection of where we’ve come from, and it may not persist over the next millennium. If everybody just sees it for what it is, fine no big deal, don’t take offense to anything. Everything you just said is spot-on; its great if a guy offers. I just remember the first time I had to pay for a guy’s meal. It wasn’t even at a restaurant; it was a take-out place. I just remember him asking me, “Do you mind going by and picking up some food for us?” and I just remember hanging up and thinking, “I have to buy a meal for a guy?” I went to the place and ordered it, and it took me 10 minutes to grab the $10 from my pocket. It was so excruciating for me just because I was raised so old-school. OK and here’s the way he was raised. He was the only boy with six other women; all highly affluent; and to him, it just didn’t mean anything.
Me: It always goes back to the childhood and how you were raised; it always goes back to it!
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The Date Smart podcast is hosted by Ambiance Matchmaking’s cofounder Taylor Wade. Twenty years ago, Taylor cofounded Ambiance Matchmaking, an exclusive matchmaking agency that has helped over 100,000 singles master their dating lives. In this podcast, she shares the same tactics and techniques with you. Mastering your dating life is easier than you think –– it’s just a matter of science and a little know-how.