Dear Men: How to Have a Perfect First Date (By Actually Being Yourself)

Forget what your therapist told you about dating for a moment. This isn’t another lesson in setting boundaries or maintaining a “perfectly curated” profile. This is about creating something real, raw, and messy: actually connecting with someone who wants YOU.

Isn’t that what you are looking for?

I’ve resisted writing this highly requested article countless times.

Why? Because while dating advice can sound universally wise, for many of my clients, it’s a roadblock — an echo of rules that simply don’t match who they are or the kind of connections that would ever work out for them. They lose decades in trying to find the right person, or trying to become the right person.

Most people don’t need more rules.

So many are caught in patterns that, frankly, have little to do with their actions and everything to do with their past. They can follow all the therapy and online dating rules they want but they will pick some warped version of their parents or their ex out of the matches ten times out of ten. They need to do somatic, nervous system work around the way they move through life. Which is why I see so many single clients.

But, none of my client matches fit any kind of mold. They haven’t been single some magical amount of time. Sometimes they break up and get back together. Sometimes they are in a relationship after one date and other times it’s a very slow take off. There are always red flags. People are messy. Connection requires vulnerability and massive change. That’s it. That is the bottom of the self-work hole. You can come out now.

Today, I’m offering something different to help you on your first dates. The dating advice you’re about to get is basic and annoyingly simple:

Be yourself.

But there’s more to it than that. So imagine rolling up to a date with your real interests front and center — not some polished ‘green flag’ version of yourself. Imagine if you never heard the phrase, “this is what women want.” Be that guy. The one that makes you smile.

No, really. If all you do if fish, play Xbox and watch sports TV then make that fully known from the start of the Internet chat. Fill the first date with fishing stories. Show your high gaming score.

Be. Your. Self.

There are some country girls I know from back home that love men like that. You have to find them. You might need to move to find them but they exist. You have to stop trying to be a “green flag” and pulling women that will HATE you into a long term connection. The longer you pretend to be everyone’s cup of tea, the longer you will actually be no ones. Or you’ll build connections you think you should have only to find them unfulfilling and short term.

Everything you do in early dating and especially on a first date is a strong filter.

Do you lean back and wait for women to ask you a bunch of questions before you actually engage in a chat? Do you only date women who largely initiate the first date? Then, you will filter out women (like me) that want things to feel super reciprocal AND women who are more passive in general. Passive doesn’t mean a door mat. It just means their personalities are a bit quieter. You will filter IN women that roll up into dating like it’s picking their next outfit. Is that the women you want to date? If it is keep going. If it isn’t… why are you doing that? Who told you that was the ‘right’ way? What do you WANT to do?

What about the woman that follows the popular advice to never initiate at all with “masculine men”?

She is trying to swing the other direction from bringing in men that felt like cold, heavy weights to her life. She wants a guy that has some ambition this time. A guy who takes some leadership, as opposed to her ex who struggled to use the calendar app on his phone. She doesn’t want to be CEO at work and at home. She was told men like to chase things. She shuts her mouth about work, puts on her low cut dresses and waits six hours before responding to texts.

But what if “that guy” she’s looking for has finally done some self work. He finally wants an equal partner, instead of playing daddy to stormy, needy women who take absolutely no lead. Those women also can’t use a calendar app. So he’s dating looking for women that take turns with him. He wants women to show up pretty equally to him in dating. He has grown out of chasing them.

They will miss each other!

They will both be sorting and filtering and using early dating behavior that will confuse the other person.

If you are a little anxious in early dating, you are often given the advice to date multiple people for long periods of time.

I know women who date multiple people for six months, forever rotating them out. My first embodiment job was for a dating program that coached this method and I tried it. It was fun. It was empowering. It was probably what I needed at that time in my life. But it didn’t bring the right men in for me. A lot of the methods actually turned my better matches off.

The theory of keeping a rotation of men on deck, is that through getting attention from multiple guys you won’t trauma bond with Todd who is going to ruin your life. Then one of these guys will turn out to be the right one.

But… guess what? If you don’t do the inner work around Todd you will still rotate him in.

Worse? You’ll never do anything squishy or authentic, like burst into tears and ask for something “too early.” Which often softens everyone up and opens the door to the guy that’s just right for you. Que accidentally saying I love you or skipping your friend hang because you can’t believe how much you miss the brand new girl.

Plus, middle of the road people who are looking for a more standard issue relationship will be turned off by this. This woman will seem confusing. She will lack the vulnerability her best matches are craving. Even men committed to clear and transparent non-monogamy would be turned off by a woman who is running a hotation.

Plus, my experience?

A lot of men and women want to focus on one person, especially after they have sex. Often before. That doesn’t make them anxious, or weak or a needy red flag you need to stomp on. I think it makes them human.

Are you filtering out people that have time to date and really want to see you as too available or too anxious? Why? Some deep inner wound I can help with OR just some bad rules?

Are you characterizing parts of your life in a weird way, that don’t represent the reality of it?

Like telling women your exes and your past online dates are your “friends”, when really you are just loosely connected to them on social media and haven’t talked in a years? Are you doing that because you were told that women like you talk well about your exes? Only to turn women off who expect men they date to be focused on their current connection?

Stop. Just be honest.

If you don’t get along with your co-parent, don’t drag the drama into your date by mostly talking about another woman, but it is ok to say, “we don’t really get along”. Being honest will also keep you from saying odd, subconscious remarks. Like telling a first date that your exes mom warned you about her before you got married. Such a trauma share. The truth leaks through in ways you don’t realize when you put it in a box.

What if the vulnerability of being yourself was the most attractive thing about you?

I had a man tell me his best dating profile was full of red flags. He broke the rules. He added edgy, weird jokes (but ones he makes constantly) and showcased a very raw version of himself. But he is an extreme person and it was ‘him’. He got less dates. But he also met “the one”. And he finally didn’t get as burned out with online dating because he wasn’t having chats with women that were going to hate him. Once he stopped being so careful it was just easier to manage.

As a by-product, he gave the few women he did connect with genuine attention.

The kind of attention he gave before dating apps existed. He treated those few matches the way he treated women in the 90s. Like they were rare. There is an appalling lack of vulnerability inside of all these dating methods and books.

Online dating can lead you to believe there are endless matches for you. But there are only endless people to date for a while. Most of which will never work out. You are a needle in a haystack. We all are.

Finally, why does your crazy sister that has never been to a day of therapy in her life do better in romance than you?

Because she’s being her crazy self on the first date. The man on the other end knows what he is getting into. She’s low-key rude to him, just like she is to you at Thanksgiving. She checks her phone, drinks too much and asks him to go home with her if she feels like it. If she wants to wait for sex until a ring is on her hand she tells him that. Hell, that’s probably all on her profile.

She didn’t read your rule books! She’s not vexing over what to do on the date or asking her friends if her outfit is ok. She just shows up as herself and expects that the man on the other end will be doing the same. She can’t play the game, because she doesn’t know a game is going on.

She’s free.

Her husband? He is never surprised or disappointed. He doesn’t accuse her at some point of “tricking him”. She might be from the scratch and dent isle part of the store. But she’s not hidden under fancy branding and shoved into tons of packaging. She doesn’t have a hard time dating. She knows not many people will put up with her. That might sound harsh but it’s kind of true for everyone.

We all have niche needs and personality traits. No one is a perfect, vanilla Barbie and Ken unless they are pretending to be.

What if you re-branded your dating profile, filled it all the way out and rolled up into first dates with your big, real life personality?

Will you get less dates? Yep.
Will you see some new things about yourself? Yep.
Will you get more rejection? Yep.
Will some dates go hilariously bad because someone was expecting you to follow a bunch of rules that you decided don’t work? Yep.

But will you have more dates with people that could actually on some planet be a good fit? Yes!
Will you treat your dates better? Yes!
Will you be more talkative and vulnerable on the dates? Yes!

Because you will have some real, shared personality traits and interests with these new people. People that actually might like you. The real you. The one you are probably rolling out around month four to six right now. Yeah, that’s scary because it’s honest rejection. Not rejection through some kind of game. But, at some point you just have to take the masks off.

How can you bring your inner world more on stage in your profile and in your first dates?

How can you be more transparent early on? What dating behavior is filtering OUT your best matches? What weird ideas have you picked up about “all women” that is likely keeping you stuck?

Is there a woman waiting for Lloyd to stand in her driveway with a boombox and you are playing the role of Mr. Big?

More of my dating articles can be found here.

…

Need help being yourself? Check out my website for courses and coaching. A new course just went live for developing basic emotional bandwidth and it’s $10.

—

This post was previously published on medium.com.

***