My 7 Easy Strategies to Make a First Date Less Awkward

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It’s no secret that first dates can be freaking awkward.

I once saw a man go to shake a woman’s hand when she was reaching over the table to grab some bread.


But what if I told you that first dates don’t have to be that awkward and can actually be fun?

A few years ago I was working as a dating coach on a reality TV show helping Kate Gosselin attract love. And what this experience confirmed for me was that when you have the right strategy and tools in your dating toolkit, you can go from being super nervous on a first date to feeling pretty good about the whole thing.

So, here are my 7 easy strategies to remove the awkwardness from a first date and have fun.

  1. Be prepared

Fail to prepare, then prepare to fail. Be prepared before a first date and set yourself up for success.

Plan out some topics of conversation so that there are no awkward silences.

I like the FORD approach for first-date appropriate topics.

F= family

O = occupation

R = recreation

D = dreams

And have an interesting story in your back pocket about your day. Little things like this will make you much more engaging and help you connect with a guy.

  1. Good conversation is less about what you say and more about what you ask

I used to put so much pressure on myself to do all the talking on a first date. But when I shifted that focus to how I can ask people interesting questions and get them talking, dates felt much easier and breezier.

One time, I went on a date with a woman and asked her a ton of questions. By the end of the date, she thought I was so interesting, but the truth was, she didn’t know anything about me because she hadn’t asked me anything!

But asking her all those questions got her talking and helped her feel connected to me. You want to aim for the right balance where you’re taking turns to ask and field questions.

Whenever appropriate, ask an open-ended question that can’t be answered with a simple “yes” or “no.” This helps the conversation flow and enables you to build a connection.

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  1. Be authentic

Yes, you should put your best self forward on a date, and of course, you want to make a good impression. But at the same time, don’t pretend to be someone you’re not just to impress a guy.

When you do this, it will usually feel awkward, and he will pick up on it. Plus, there’s only so long you can wear a mask before he sees the real you.

I once went on a date with a woman, and she mentioned her ex was an adrenaline junkie and that she wasn’t into any of that. If you know me, you’ll know I am also a huge adrenaline junkie (motorbiking, kite-surfing, you name it).

In that moment, I could have downplayed it to stay on the same page as her, but I chose to be authentic and own that I love that stuff.

Needless to say, we didn’t go out again, and that’s okay.

  1. Be present

Another strategy to make a first date less awkward is to try and stay in the moment with him.

Resist the urge to dwell on your past dating track record or get caught up in a daydream about the future. When you do that, you take yourself away from the present, which blocks you from building a connection.

Make a conscious effort to stay in the moment, and you will feel more relaxed and engaged in the conversation (this is part of Little Love Step #4).

  1. If something awkward happens, own it

A first date is two strangers meeting and hanging out for the first time, so sometimes this will be awkward, and there’s nothing you can do about it apart from owning it!

So if you spill your red wine all over the table (or his crisp white shirt), or you end up snorting while laughing at one of his jokes, own it.

You might think you’re going to die from embarrassment, but I promise it’s not as bad as you think it is, and if you can laugh about it, guys will find that endearing.

Plus, it’s a great way to break that first-date tension!

  1. Remember that he’s probably nervous as well

According to a 2019 survey, 47% of the population consider themselves shy. That means almost 50% of people will feel nervous on a date.

And I think there’s extra pressure on guys to “perform” on a date.

So if the man you’re on a date with is a little quiet or withdrawn at first, be nice about it. Don’t get frustrated with him. See it as a challenge to get him to open up and start talking.

If you’re ever unsure about a guy after the first date, always give him a second chance.

  1. Just have fun

My final strategy to make a first date less awkward is just to relax and have fun!

It’s easy to make dating this super serious thing when you’re serious about finding love. But don’t bring that serious energy into your date.

Enjoy yourself, laugh, flirt, and focus on having a good time and a new experience.

What is the most awkward thing that has ever happened to you on a first date? Tell me about it in the comments below!

What do you think? Share your thoughts below...

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adrian mallin
8 months ago

What’s wrong with Clam Chowder?
You’re great – Only weirdness on a first date was when I told him I lied about my age – he became adamant – he literally got up and left the date – and the waiter watched the entire scenario – about 20 years younger than myself – and instead he asked me to wait for his shift to be over – and he took me out – it was a GREAT evening!!~

8 months ago

I wasn’t drinking on the date but the guy I was on a first date with was getting hammered and I couldn’t stop staring at whatever was stuck in his teeth, the bill came and he started freaking out about it to the waitress which was completely embarrassing since he was the reason the bill was 40 and I offered to pay for my meal since it obviously was a problem and as I left I wasn’t going to go out with him again and he had the nerve to lick my neck as I gave a hug before leaving… Read more »

8 months ago

On a date luncheon. The guy may only have two bites of his meal. Waitress. Comes over many times an ask him what’s wrong with the meal. He’s so uptight. He can’t eat.

8 months ago

these are great tips! Thank you. I’m going on my second date after 22 years tomorrow. The first date was hysterical! I brought my favorite couple along with me to meet the guy who said he was 68 in his profile on dating app. Upon meeting him, his photos were clearly not current ones. He was the biggest braggart too, he answered our questions, never asked us one – and if we did share something about ourselves, he would interrupt and turn the conversation back to his diarrhea of the mouth. Once he said he was in the Viet Nam… Read more »

7 months ago

If he cares enough about you, there won’t be any awkward awkwardness. On the contrary, he will show you a guy who is lovable and pampers you.

Color Tunnel

6 months ago

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