Mar 4, 2014

10 Tips For Having Stress Free First Dates

Let’s face it… dating can be awkward and nerve-racking, especially when it comes to first dates.

The two of you arrange to meet in a public setting to casually feel each other out and see if you want to continue spending more time with each other past the original meeting.

You can stumble in to a date unprepared and racked with nerves, or you can plan ahead and remove a lot of the unnecessary stress that comes with the initial phase of the mating dance.

Here are ten tips to help you have better, more stress free first dates.

1. Call It A Date When You Set It Up

There is a trend right now to play the cool card up front and leave it ambiguous as to whether or not it’s officially a date (as in “Hey, want to grab coffee sometime?”… LAME!)

Ambiguity isn’t sexy. Being intentional and direct is sexy.

If you know that you want it to be a date then call it a date. As in, “Hey, you seem really interesting and it seems like we would get along quite well. What’s your week looking like? I’d love to take you on a date one of these nights.”

If you are honest with yourself and your date about what your intentions are then you can leave all of the brain-clogging “Is this a date? Is this not a date?” talk for your former self.

2. Be Able To Upgrade Or Downgrade Your Date

The old saying “Expect the best, but prepare for the worst” applies here.

Have a plan, have back up plans, and have alternate plans. Depending on how well you and your date get along, you will want to have the ability to upgrade or downgrade your date at any time.

Your date turns out to be really boring and uninspiring? Downgrade by cutting the date off after drinks, offering a ride home if you have a car and they don’t, but don’t offer false hope if you don’t want to pursue this further. If they don’t accept a ride, you can guess that they were uninspired with you as well!

Your date turns out to be one of the most interesting people you’ve ever met and your conversational chemistry is off the charts? Upgrade your date by going to the next, more intimate stage of the date that you had planned (going to an art class, dessert bar, or romantic lookout point).

It might sound like a lot of work planning for multiple contingencies, but it will allow you to let go more fully during the date.  Yourover-preparedness will pay dividends in terms of how relaxed you feel on the date.

Besides, since when is being too prepared a bad thing?

“The more you sweat in peace the less you bleed in war.” – Chinese Proverb

3. Pick The Right Place

Pick a location that you feel comfortable in, but pick something that isn’t your regular spot where everyone knows you. If you seem to know everyone there then you run the risk of your date either feeling less important, or they might assume that you take all of your first dates there.

Meet on mutually beneficial territory that you would both enjoy. Whether you are finger painting, bowling, or grabbing dinner all depends on you… this all comes back to personal taste.

Where would you both feel engaged by your surroundings, with a bit of curiosity about your surroundings? Bonus points if the environment has built in conversational points to it. Also remember to pick a place that isn’t too loud. You want to have conversation flow easily, not be strained while shouting over the house band.

4. Be Intentional About Your Day Before The Date

Do whatever it takes for you to be in a good headspace. If you drag yourself through a listless and boring day then you will carry that unattractive energy into your date.

Go to the gym that day. Tick a bunch of random tasks off of your to-do list. Groom yourself a bit more than you normally would. Dress in clothes that make you feel like your best self.

Do the kinds of things that get you in a good place so that you can walk in to the date feeling confident, and like you’ve prepared all that you can. Then, let go of your day as you walk in to the date and enjoy the mindset of “Alright, let’s see how much fun we can have for the next little while. My only expectation is that I will get to see the world from another person’s perspective and we might just happen to have some cool things in common. Let’s find out!”

If after your awesome day you still notice your heart beating rapidly as you wait for your date to show up, something that I have done many times successfully to calm my nerves right before a date is to do an exercise called box breathing. Box breathing is when you inhale slowly through your nose for a count of four, hold your breath for four seconds, exhale through your nose for a count of four, and holding your breath for a count of four before you inhale again. Do this ten times as you wait for your date to arrive and you’ll notice your heart rate calm noticeably.

stress free first dates

5. Un-Plug Completely

Put away your phone. Like away away. Full on airplane mode and out of sight.

This is such a simple common courtesy and it shows your date that you are serious about getting to know them without needless distractions. The only phone calls that I can imagine you would need to take would be things that should indicate that you shouldn’t be on a date in the first place (your wife is 8.5 months pregnant, or you have an exam the next morning and someone is calling to give you their notes).  So put the damn thing away. Even if you think a call is important, surely it can wait a couple of hours.

The future of your entire intimate life could depend on it.

6. Come With A Few Stories Prepared

What if your date takes a while to warm up conversationally?

The best dates have multiple stories prepared in case they need to have some backup conversational fodder as a jumping off point for their guest.

Don’t prepare stories to the exact plot point and come across as rehearsed and showy. But do be aware of the things that have happened to you in your life that people tend to find interesting in case you need to switch gears when a conversational threads dies off.

7. Have Fun, At Any Cost

One of the biggest reasons that people are nervous heading into first dates is because they are overly focused on how they will be perceived.

People worry “Will they think I’m clever/funny/interesting/attractive enough?”

Remind yourself that someone who is meant to be with you long term will like you even if you show up with some nervous energy in tow because they will be able to see the real you through your nerves. Maybe they will even feel flattered that you are nervous because you really care, which is certainly better than a lack of interest in the impression you make. Focus your intention on having fun above all else. If you try to see and understand the person across from you, and you do so from a place of playfulness and curiosity, you are bound to have fun with them.

8. Embrace The Awkwardness

If awkward topics happen to naturally come up (messy break ups, deaths in the family, differing religious or political views, etc.) then don’t try to sweep it under the rug.

By trying to subtly ignore the fact that it’s awkward, you give it more awkward-power. Call attention to it and steal away it’s awkwardness.

Say, “so what shall we talk about next? Religion? Politics? Our exes?” Saying this with a cheeky tone lightens the mood and allows you to continue on with lighter banter.

stress free first dates

9. Take Care Of The Bill

In my fifteen years of serial monogamy I have learned one all-encompassing rule about the bill… don’t let it cause awkwardness.

An awkward payment process can easily un-do the magical momentum that you’ve built up throughout your date if you handle it poorly.

If you initiated the date, you should expect (or at least be fully prepared) to be footing the bill for the entirety of all the activities that you may end up doing.

So pick it up. Without awkwardness. Don’t call attention to the fact that you’re doing it or that you’re a special person for doing it. Just do it. If you set up the date, it’s on you. Assuming you are a hetero guy reading this article, chances are she spent more on her physical appearance (clothes, make up, jewelry, etc.) and you spent less than half the amount of time getting ready than she did. Show your gratitude and just pay the damn bill.

10. Sex, Or No Sex?

Before you go on your date, ask yourself whether or not you are comfortable with sleeping with them on the first date. Don’t refer to society’s expectations of you. Ask yourself before the date whether you are in an emotionally available enough place to want to be physical intimate with someone right away, and how that sits with you.

I have many male and female clients who are totally willing (and unwilling) to sleep with their new love interest on the first date. Cosmo and Maxim don’t know anything about you. The only right answer is the one that your heart honestly tells you.

So check in with yourself before you meet them to see where you stand on the matter on the day of the date.

Take A Deep Breath

Dates are meant to be fun. Plan ahead, be honest with your intentions, be open to whatever happens, and the date will be fun (or at least a good story to tell later on).

Dedicated to your success,


Ps. If you want an even more in-depth analysis of ideas for what to do on a date, check out my book 50 Powerful Date Ideas (on Amazon), or grab it here in PDF format.



See All
The Most Important Thing About Getting Into A Relationship
Sep 16, 2014
Jordan Gray
The Most Important Thing About Getting Into A Relationship
If there’s one thing I’ve learned about what makes a new relationship work or not, it’s the following… Ask yourself this question to know whether or not you should be dating the person you are and your entire life will benefit. Do you feel compelled or do you feel cornered? So...
Continue Reading
The Top 10 Best Articles Of 2016
Dec 26, 2016
Jordan Gray
The Top 10 Best Articles Of 2016
2016 was a massive year of growth for me. Many big wins and many big challenges. On the wins side... I helped more people this past year than I had cumulatively helped in my previous six years of coaching combined, I cultivated a deep sense of community for the first time in my adult life, I lived...
Continue Reading
3 Ways To Set Up Your Single Life For Success In Dating
Jun 16, 2014
Jordan Gray
3 Ways To Set Up Your Single Life For Success In Dating
It's all too easy to blindly fumble around from dysfunctional relationship to dysfunctional relationship. But does that mean that that's your only option? There are things that you can do in the space between your relationships that will set you up for success in your love life. Miss these, and...
Continue Reading
Are You The Reacher Or The Settler?
Oct 22, 2013
Jordan Gray
Are You The Reacher Or The Settler?
Are you settling in your relationship? According to Dean C. Delis, author of The Passion Trap, every relationship has a reacher and a settler. A reacher is the "one-down" partner who is dating someone who is somewhat out of their league. The settler is the "one-up" partner who could do better,...
Continue Reading
How To Make Your Long Distance Relationship Work
Mar 31, 2014
Jordan Gray
How To Make Your Long Distance Relationship Work
Let's face it… long distance relationships aren't always a walk in the park. Whether you're playing duelling time zones, trying to schedule your next phone call, or just miss cuddling up with your significant other, it can often feel like a challenge to maintain an emotional and sexual connection...
Continue Reading
The 14 Day Relationship Revitalizer: A Free Step-By-Step Guide
Jan 18, 2016
Jordan Gray
The 14 Day Relationship Revitalizer: A Free Step-By-Step Guide
A few weeks ago, I received a first-of-it's-kind email in my inbox. A long-term client of mine (named Joseph) told me that he and his wife of twelve years were going to take an extended vacation with each other. Their shared business was essentially running on autopilot and they had more than enough...
Continue Reading