Life Unchained: Pulling Off the Perfect First Date
Date planning is one of the biggest topics that comes up in the men’s focus groups I work with. Especially with younger men who maybe don’t have a lot of experience showing a woman a nice night out.
Because let’s be honest, as men, there are tons of questions that go into asking for the date, planning it, being present in the evening, and gauging just how interested she is in a second date.
I know this is the part where I’m supposed to brag about my magic touch with the ladies. As a grown-ass man, I don’t do that. Let’s just say at age 50, I have zero complaints about my love life.
Along the way, I’ve learned some dating truths and techniques that will give you the best chances of showing a lady a special night or give you clarity on just how interested she is.
What Is a Date Night?
For our purposes here, we’re going to look at a classic first date. The sort of thing where you both go out to eat, and there’s some other form of entertainment. It might be going to a comedy club, playing some mini golf, or catching a movie.
It’s the most common type of first date.
In the real world, I think you’ll get the best results from a shared experience, but that deserves its own separate article.
The Getting to Know You Phase
The week or two leading up to that first date is arguably the most important part of your first date leading to a second or third. You probably met on a dating app, and ideally, she slid into your DMs.
As a personal policy, I don’t swipe to women. They swipe to me, which tells me right off the bat that she’s authentically interested in me from the snapshot on the app. I don’t want to be like those desperate dudes out there, who are constantly worried about the hundreds of other dudes they’re competing with.
During this get-to-know-you phase, you want to communicate some degree of emotional safety. This means being a good listener when she reveals something vulnerable about her life, and it also means not being judgmental.
If she reveals a personal flaw or something she’s working on, you don’t need to jump in and tell her she’s perfect. This comes off as the same kind of inauthentic compliment all the other guys are dropping in her inbox.
A lot of times a woman shares something personal because she wants to see how you handle it. Listen to what she says without trying to fix her, lecture her, or turn the conversation into your own therapy session.
When you try to “Fix” the thing she’s challenged by, it can accidentally come off as you making her feel like she’s not capable of taking care of herself.
Don’t position yourself as this hero who is going to come in and rescue the damsel in distress. Demonstrate that you have the potential to be a supportive future partner but simply be supportive of that thing she’s working on. And always keep the conversation trending positive.
When to Ask for a Date
When you’re getting to know a woman leading up to a date, you don’t want to become her new pen pal. If she lives within 60 miles of you, you should ask for a date in 7 to 10 days of her sliding into your DMs.
How to Ask for a First Date
When you ask a woman on a first date, you want to come with a confident plan. Don’t say “Hey, uh… I was wondering if maybe you’d like to go out or something Saturday night.”
Instead, say “Do you want to go out to dinner Saturday night, and catch a comedy show afterward?”
Proposing the Date
Ideally, you want to suggest dinner and some form of entertainment that are within reasonable walking distance of each other. Being able to navigate with each other, walking city streets, crosswalks, and you choosing to walk on the traffic side of the sidewalk. All that stuff might seem small, but it sends a subconscious message about your potential for teamwork.
Offering up two restaurants near the entertainment also tells her that you’re happy to accept her feedback into the date.
This shows planning, purpose, and leadership without coming off like a domineering dude. You’re asking for a planned date, and by offering two potential restaurants or a different form of entertainment, you’re communicating that you’re open to listening to her interests.
How to Prepare for the Date
I see date prep as a multi-level thing with a few key points that happen a few days in advance.
Facial Hair and Grooming
I have a goatee, and I know it’s particularly bristly right after I trim it. So I trim it a little bit shorter than usual 48 hours before the date. This gives it time to soften a little in case I get the chance to go for that goodnight kiss.
Then I shave my head and face an hour before the date. That way if I do nick myself, I’ve got time to get it under control.
I like to put antiperspirant on each armpit and a stripe of deodorant on my chest hair. So when she goes to give you that hug hello, her nose near your chest is going to pick up the smell. And of course, you want a freshly laundered shirt that was washed with fabric softener.
Physique
I work out, I’m in great shape for a man my age, and I do make an effort to show that off a little bit. A man who takes care of himself physically sends a message of self-respect and discipline that’s attractive. And yes, muscular arms and strong shoulders do help.
The mistake a lot of guys make is that they try to bang out a bunch of curls right before the date to “Get a pump.” However, this fades really fast.
Instead, I like to put in a workout 24 hours before the date with a lot of medium to lightweight lifts and high reps. This causes an inflammation reaction in your muscles, making them look a little larger. And when you get that hug at the end of the night, she will notice the firm feeling.
Clothing
It pretty much goes without saying that you need to dress appropriately for the evening. Business casual is as fancy as you should get for an indoor date in the cool months of the year. Whereas for a summer outdoor date, you can get away with a nice pair of cargo shorts and a polo shirt.
If there’s a puff of cool air in the forecast, I have a tasteful dark blue Spyder jacket that I’ll wear to start the evening. Then when it gets cool, I’ll offer it to her in that gentlemanly way.
NOTE: Do not have anything remotely incriminating in the pocket of your jacket to start the night. Most women love to snoop, and if she finds a sachet of Viagra, and an expired condom hiding in the coat pocket, you’ll send the wrong message.
Preparing for Conversation
You should absolutely prepare 2-3 humorous anecdotes for a first date, each sprinkled with some self-deprecating humor. Don’t vent about work, your co-workers, or problems going on in the background of your life.
Now I only date women who swipe to me, which means they’ve selected me from the crowd in advance. If you swiped to her in the dating app, you might want to be a little more careful as it likely means there are other guys in her DMs that she’s measuring you against.
I like to have a story about how I grew up. Something about the emotional intelligence I picked up from my parents. Showing that you understand feelings and how they affect you is incredibly attractive to women.
A travel story mishap story is also handy. Other guys she’s gone out with have probably tried to impress her by talking about sunsets, waterfalls, or exotic locations that blew them away.
Instead, tell the story about the time you accidentally ordered the giant family-size salad at a Nashville steakhouse because you read the menu wrong.
Most men struggle to be humble on a first date and try to brag about their adventures. If you demonstrate the ability to laugh at yourself. It shows you are emotionally accessible, and that you’re less likely to judge her flaws.
Explaining a hobby that you’re truly passionate about is also a great conversation topic to be prepared for. For me, it’s about fitness and working out. Shows that I take care of myself and that I practice a level of self-respect and personal discipline most middle aged men don’t have.
For me, it’s also tied into losing my parents and how it inspired me to prioritize my health.
NOTE: Do not talk about playing video games, getting drunk bros, or the things you used to do with your ex.
Being a Good Listener
The art of truly listening to someone, especially a woman on a first date, who’s probably nervous herself, requires focus.
The number one thing you want to listen for is some sort of shared experience. Her favorite park she played in as a kid “Wow, I used to ride my bike past there once a week back in the 90s. I wonder if we accidentally met then and didn’t realize it.”
Maybe your kids go to the same school, and you have a shared gripe about the music teacher. The truth is, she swiped on you or agreed to the date because she seems things you have in common. When you pick up on them and comment on them, it creates connection.
Developing a Layered Dating Strategy
The typical first date most couples go on averages around 2 hours, which I don’t think is enough time to create a lasting impression.
My average first date is around 6.5 hours, and I almost always have a second date. The trick is to always have something to add onto the date. This is a suggestion that seems to come out of nowhere to gauge her interest. Yet, as a thoughtful date planner, you already researched things like dance clubs, acoustic music performances, a late-night poetry session or a mini-golf course.
Let’s use my dinner and a comedy show example from earlier. I know my downtown area very well. On Saturday nights when the comedy show ends, the acoustic music lounge starts their first act.
If you present this add-on, and she says “Yes,” you’re not only extending the date to make a more meaningful connection. She’s also telling you that she’s interested in getting to know you further.
This also spares you going home later and wondering if she’s interested enough to go on a second date. In my experience, any woman who says “Yes” to that add-on after the show has a 90% chance of saying “Yes” to a second date.
And that takes a lot of the pressure off you for the rest of the evening.
Make sure you’re armed with options. After the acoustic music, maybe it’s a stroll along the river. Perhaps it catching a nightcap at the nearby dive bar, or even a late-night snack at a taco truck.
NOTE: Don’t take it too seriously if she turns down the second add-on, as the night does need to end at some point.
It’s the very first add-on that matters as a gauge of her interest. I’ve even so far as to excuse myself from her hotel room at midnight. Then say “Hey, do you want to go thrift shopping tomorrow?”
And we add on to the next day.
In my case, where I only date women who swipe to me. She’s probably wondering just how interested you are in her. So, when you’re offering all these add-ons to extend your time together, it’s also sending her the message that you truly want to get to know her.
Final Thoughts
In my 50 years on this planet, I’ve been on a lot of successful first dates. I stand by the add-on concept both as a way to show your leadership as a man, as well as to gauge her interest.
Assuming you’ve planned wisely, listened to her input, and demonstrated a sense of emotional safety through the get-to-know-you process, chances are good she’ll say Yes to that first add-on idea. This gives you the confidence to assume that there’s probably going to be a second date.
Preparing your body and mind, as well as coming prepared with humorous anecdotes, will show a lot about who you are without having to tell her your life story in hopes of impressing her.
Regardless of when the date ends, always make sure to send her a text message thanking her for the wonderful evening. Mention how you’d “Love to do it again sometime.”
Frequently Asked Questions
The following are common questions I’ve come across in men’s focus groups that might help you dial in your first date style.
Is meeting for coffee a good first date?
If you’re a natural conversationalist like me, meeting for coffee can be a great start to a date. The trick is to schedule it in mid-afternoon at a location near a restaurant. So, if the coffee conversation goes well, you can drop that add-on question to move it to dinner.
Are drinks a good add-on to a date?
I’m a sobriety advocate, so I never drink when I’m on a date anyway. In my experience, a truly high-value woman is turned off by a drunk man. So, a nice glass of wine at dinner, a craft beer that you sip on during a show, or a single nightcap might be acceptable. Anything to “Catch a Buzz” or take the edge off is unwise.
Should I go for a kiss on the first date?
If she says “Yes” to a second add-on, then there’s a 90% chance that she’ll say “Yes” to a kiss at the end of the night. Otherwise, I’m content to settle for a long hug at the end of the first date.
Who should pay on the first date?
I always go into every first date assuming that I’m going to pay for everything. If she offers to pay for something, I don’t put my foot down. I just never expect her to pay for anything.
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