How to Ace a First Date

First dates can be hard to plan! From what to do, where to go, and how long to wait to make plans, we have some key tips to help you ace your first dates. Join Master Certified Matchmaker Genevieve Gresset and Certified Dating Coach/Matchmaker Heather Drury as they give their advice on how to ace your first date, based on their many years of matchmaking experience.

Heather: All right. Welcome back. We’ve got another wonderful letter to work through, and I think our matchmaking expertise is going to come in handy with this letter.

Genevieve: Go ahead. I’m ready.

Heather: Okay. So the subject line is: “What do I do during that time between asking someone out and actually meeting up with them?” Well, they go on to say: “I was set to go on a date with a woman this week, but I actually caught a bug that’s going around. So we’re more likely meeting up on Saturday just for casual ice cream (in college and trying to save money).” Well, either way, ice cream is just cute.

Genevieve: Ice cream is good anytime!

Heather: Exactly! Who cares about money? Go get some ice cream. “The conversation is going at a pretty slow pace during the first two days, we talked a bit more and now it’s just a text here and there throughout the day. I just don’t want to have her lose interest. But at the same time, I hate texting and I don’t want to burn up the conversation topics over text.”

Genevieve: Correct, you don’t. This is just music to our ears.

Heather: Wouldn’t you say? When I was like, okay, we’ve got some good advice here. So as your certification teaches us, dive in, please. This is really important. The gap between getting the interest and then getting the date. What do we do?

Genevieve: Well, first of all, don’t leave a gap. I mean, also, he’s been unwell, so there’s a gap for that reason. But try and meet up as quickly as possible, because what can happen in that gap? Someone can go off and meet somebody else or they can just switch off altogether and think, “You know what, I’ve changed my mind. I don’t want to do this.” So my advice to anyone who is starting to date and has got some interest is get out there, don’t talk, don’t text. Just, you know, set the date up and go on the date. Meet each other, because then you’ll have loads to talk about. Then you’ll know. But the other thing, you don’t ever know from the first date. You need to do a couple of dates before you really know whether you want to pursue a relationship or you don’t want to pursue a relationship. I think it’s really important that you invest that time and show that you’re enthusiastic and keen. You know, the poor woman might think, “Hey, you know what? He’s not set another date. He’s not interested in meeting me.” So if you are interested, let them know and get out there and get on with it. So really, is that simple.

Heather: Boom, done! Exactly, and scene. Just kidding! I love that because I think one thing we have to really realize as normal human beings, dating brings out the weirdest emotions inside of us. So if that gap gets bigger and bigger and bigger, insecurities can tend to weasel their way in.

Genevieve: And you’ll never get that date. It will never happen. How many times do we say if you leave over a week, it’s unlikely you’re going to meet?

Heather: Another thing is going to come up and then ANOTHER thing is going to come up and it’s like, “Well, we didn’t meet in the first place anyway. I’ll just go on to the next person.” That’s kind of what online dating has bred is this “Okay, next!” mentality.

Genevieve: Or “I’m giving up altogether. I’m just taking a break, I’m burnt out. I need to detox from dating. Time out.”

Heather: “Time out, I’m done.” Exactly. The other thing too I want to recognize I think we both had this mutual reaction. Do not underestimate the power of an ice cream date for the first date. Let’s go into that. What should the first date typically look like, Genevieve?

Genevieve: It should be fun.

Heather: Yes.

Genevieve: You know, the last thing you want to do is sit and be interrogated. Someone just asking questions. You don’t want to do something like a big romantic meal either. That puts too much pressure on both of you. Then there’s the awkwardness of “Who’s paying the bill, are we splitting the bill?” The first date should be short. It should be something that’s fun. I love an ice cream date! I often say go for coffee and cake. Something that you can do that can be a bit flirty as well. Nothing more flirty than some ice cream. It’s one of those things that whatever your first date is, you don’t want it to be formal. You don’t want it to feel like you’re at a job interview and someone’s all of a sudden going to get your resumé and start questioning you on what the last ten years of your life has been. You want it to be easy. I mean, bowling’s a good one. Something that you can share together and have a shared moment that you can talk about, that you can enjoy. Choosing different ice creams, “Oh, can I just taste this one? Here, Have a little taste of this one.” You can make it playful. You can make it fun. You can get to see if you’re on the same wavelength. Being mutually curious about each other. That’s what you’re looking for. The first date is not about, “Am I going to live with them for the rest of my life? Are we going to grow old together? Are they tall enough? Are they short enough? Are they sat in isolation enough?” It’s not about any of that. It’s “Am I curious enough to see them again. What do I like about this person?” We can all set ourselves up to fail. We can all set ourselves up to find fault with everybody. So set yourself up to succeed when it comes to dating. Keep it simple. Look for the three things that you like about them. “Wow Heather, you’ve got a lovely eyes. Your hair hair’s so shiny and you’re such a happy person. I really want to get to know you better.” It’s really that simple.

Heather: “I love you. Marry me.”

Genevieve: “I’m out of here.” Someone’s going from 0 to 60!

Heather: Yeah, but I love that. Doesn’t that make it so much more, I don’t know, fun? When you go and you get ice cream. “Why did you choose Strawberry? I don’t know. I’ve just always loved it. It reminds me of my childhood. Oh, my gosh! That’s so great! Why did you pick this topping?” It’s just so creative and fun, and outside the box.

Genevieve: It is, and also something like going for a walk. Go and explore something new together. You could even say, “Hey, I’ve never been to this part of town before. Can you be my tour guide?”

Heather: I love that!

Genevieve: Or go somewhere that neither of you have been, and be tourists together somewhere. It’s a shared experience, and what we know scientifically is if people share experiences and they laugh and they connect, there’s far more of a chance that that relationship will take off in the long run, compared to sitting having dinner and just being a bit boring, quite frankly.

Heather: Who the heck made up this rule or this stigma that we have to have like a fine dining experience with a big glass of wine and a giant steak on her very first date? I need to meet that person and say, “You messed us up, buddy, no more of that!”

Genevieve: I mean, to me, there’s nothing worse. You’ve got that pressure of going somewhere. I remember once going on a date and they’d ordered spaghetti pasta for both of us. All I can think about is “Oh my God, I’m going to come out of here and look like a right mess. Food going to be all down me I’m going to have bits stuck in my teeth and I’m just not going to leave a good impression.” That pressure is just too much even for us experts.

Heather: Exactly. One thing I will encourage the knowledge of is that I know that often times men might say, “Oh, she didn’t order anything, she didn’t eat anything!” We are nervous, and when we’re nervous, our bellies don’t allow us to fill it up and have a big giant meal. So taking us on a walk or getting a thing of ice cream, no matter if you’re in college trying to save money or you’re a “bazillionaire,” it does not matter your income bracket. Go do something that just allows the nerves to exist, but a playful way to work around them and not just stuff food on top of the nerves because that’s just never fun.

Genevieve: Picnics are great fun too! Another thing to mention is don’t ever go to a date to go and get drunk and have loads of beer or wine. I think one or two glasses is perfectly adequate. Anything more than that, you’re opening yourself up to potential complications. Just keep it simple! People overcomplicate dating, they really do. They put a lot of emphasis on getting the date. Right or wrong, there’s nothing nicer than someone standing in front of you and saying, “You know, I’m really nervous. I’m acutally really nervous. You look lovely. You look better than I was expecting, and that’s making me feel nervous.” I am. If that’s how you’re feeling, be real about it, because there’s nothing more endearing and someone hopefully will turn around say, “You know what? I’m nervous too.” So let’s throw away the nerves and let’s just enjoy this time together. What’s the worst thing that can happen? We end up as friends or we never see each other again. That’s the worst thing that can happen, right?

Heather: Both of those outcomes are okay!

Genevieve: Or we end up being the best of friends and living happily ever after.

Heather: Exactly. Exactly. Both are amazing. We overcomplicate as a society that very first meeting, that very first date. We’ve programed ourselves to believe that if it’s a powerful first date, that means I’ve set myself up for a powerful dating relationship experience with this person. But actually it does kind of the opposite.

Genevieve: You want it as simple as possible. I think the best dates people report back to us on, and I know certainly for me, it’s the simplicity. It really is the simplicity of the date where you can be comfortable, be yourself and enjoy each other’s company and can get curious about each other. That is it!

Heather: That’s the name of the game. That’s it. That’s all you have to do. And yes, you’re going to get sick and there’s going to be interferences inbetween the time you want to meet somebody and then something happens. But as much as you can, meet as promptly as possible. Let’s just make sure that the meeting happens in person so you can just be curious, shake hands and see what happens next. You never know. What is so great about this question, it is such a matchmaker question with so many wonderful tips to give. I think for people that are serious about dating, they don’t want to play games.