Hey Single Men- Here are Five Dating Mistakes You’re Making

By Tess Challis

Author of Food Love: Nourishing Yourself, Your Family, and the Planet

Hey there, single guys! Do you ever get frustrated and wish someone would just tell you what you’re doing wrong? I mean, it’s like the spinach-in-the-teeth thing sometimes. You go out for dinner, wonder why your date is looking at you funny, and then find out later your teeth have green stuff stuck in them (and incidentally, she should have told you to check your teeth—that’s just rude).

However, what’s up with her looking at you funny when there’s nothing in your teeth? What’s the “green stuff” you’re not able to see with a mirror? I’m about to share a few truth-bombs you may not have known. So grab a cold one and read on. Here are the top five dating mistakes you’re making.

OK. So, what are those five mistakes you’re making, guys?

  1. First impressions really matter. Don’t look too “truthful” on your first date.

I recently had a first date with someone who said this to me beforehand: “I want to have a little time after work before we meet up. I’ll never have another chance to make a first impression on you.” Dude. This guy was already impressing me, even before our date. Why? This one little sentence told me the following – I was important enough for him to make a solid effort. And he was going to be all cleaned up and looking nice. Both of these things go a long way with me.

Unfortunately, some guys have a misunderstanding that their dates should just see them “how they really are.” They don’t want to mislead them by looking all nice and stuff. I mean, sweat pants and sloppy hair are their day-to-day reality, so why hide it? Um, bro. No. I love honesty as much as the next person, but come on. Make that good first impression. It matters.

Oh, and by the way – the guy I mentioned earlier also happened to ask me if I preferred clean-shaven or scruff. Wow, how thoughtful! And yes, I’m going on a second date with him. He did a good job on all five points in this article, without having to be told, so yeah. Second date? Heck yeah!

  1. Don’t be afraid to show some cards.

This is a continuation of what I was saying in the first tip. It’s A-OK to let her know she’s important. You will get nowhere by playing it cool and making her wonder if you care. Sure, you may attract a few people with this stuff. There are those who subscribe to the “I don’t want to be part of any club that would have me as a member” group, but that’s not exactly a set-up for lasting romance.

You want someone who won’t play games, right? You want someone who will be nice to you? Say nice things to you? Do nice stuff for you? Yeah, of course you do.

 Then, start that ball-of-nice rolling by telling her some good stuff. Let her know she looks nice. Let her know this date is important to you. Don’t be scared. You’ve got this. Even if you feel a little nervous, she’ll appreciate the kindness and openness (and if she doesn’t, she’s not the one for you anyway).

  1. You’re failing on the follow-up.

Again with playing it cool. No, we’re not having that, thank you. If you’re interested, let us know! If we have to play detective, we’ll get bored and move on. Playing detective is fun if there’s a prize involved and we get to do it for maybe an hour at a party. But it’s pretty boring after that, and contrary to the tough-guy stuff you’ve heard, most women want someone who properly follows up. Don’t play the “I’ll call you in three days” game. It’s stupid. If you like us, call us the next day. Don’t let a day go by without a text or a call. Of course, being desperate and needy isn’t a turn-on, but solid follow-up is. Stay in touch and let us know you’re interested. Be that guy. We like that guy.

  1. You need a Conversation 101 crash course.

Oh, and by the way, this one is easy (but oddly, almost no one actually does it). Want to know the secret to being a great conversationalist, especially on a first date? Ready for this one? It’s HUGE. Can you guess what I’m about to tell you?

OK, here goes: You ask her questions. And then… you listen to her response. Yep, this one is pretty simple, but it’s also pretty rare. How many men have I gone out with that actually have this one down? I’d say maybe five percent. The other 95 percent just talk about themselves incessantly. Yes, we get that you’re fascinating. And yes, we do want to know about you too. But come on. If all you do is talk about yourself, we’ll assume you’re not really interested in getting to know us. And we’ll also assume you’re self-absorbed (even if you’re not).

And no, this doesn’t mean that the talky-talkers are bad guys. It just means they’re not paying attention. And yes, perhaps you’re talking too much because you’re nervous and making mindless chatter. But, man, that’s not the impression you want to make. Stand apart from the crowd and make her feel special by asking her questions and listening to her responses. Simple, but effective. You’re welcome.

  1. You’re way too into us way too quickly.

Yeah, this one may sound like a contradiction to some of my previous advice. And yes—we do want you to share your feelings, give us compliments, and follow up daily. However, if you’re too into us too quickly, it might register as a red flag to, say, someone like me. I’ve had this happen three times over the past year, and I’ve had the same result all three times—lots of fizzle up front, and then boom. Nada.

I’ve found that if someone is freakishly into me too quickly, there are three possible reasons why (and none of them are good): 1. Maybe they’re actually into their fantasy idea of who I am, and hence not seeing the real me. 2. Maybe they don’t have enough sense of self, and are a little on the co-dependent side. 3. If they’re not really getting to know me (and, ahem, not asking questions like we just talked about in #4) before professing their adoration, their feelings can’t be genuinely that deep. And, again, fizzle.

So, yes, please do show affection, make us feel important, and let us know you care. Yes, yes, yes! But, keep your sense of self, and get to know us before telling us we’re the love of your life, or calling us your “unicorn.” Walk that fine line of showing your cards, but not throwing them all up in the air like a crazy person.

OK guys, I hope this helps! Just remember—be yourself, show up looking your best, let her know you care, ask questions and listen, and find that balance. You should be well on your way to making a great connection if you follow these steps. You go, bro!


We hope these tips will help you make the most of your Veg Speed Date experience—and hopefully connect with someone wonderful! Find out where the next Veg Speed Date event is located and be sure to sign up in advance, as seats sell out early!

You can also check out this guide on what to expect at your first Veg Speed Date event.


Tess Challis is a vegan chef, wellness coach, and five-time cookbook author and can be found on tesschallis.com. She’s a big fan of Veg Speed Date as well, and hopes to host an event soon! Guys, be sure to use these five tips on your speed dates as well – you only get one chance to make that first impression.