Dating at 40 versus 30 is an entirely different ballgame. I should preface by saying I’m actually 38, and in my mind — not completely single.
Right now I’m going through a very difficult stage of my life — and I wanted to write this article to help those of you 40 year olds who may be going through the same type of issues.
Back when I was 25 years old, I was single and living a fast urban lifestyle. I lived for the San Francisco nightlife and the addicting dopamine rush that came with going out every weekend trying to meet new women. I really didn’t have any dating standards back then, and looking back — didn’t really know myself very well.
Nothing really changed until my 30th birthday. I remember that day like it was yesterday. I rented out the top floor of a well known bar/club in Lower Nob Hill and invited 20 or so of my friends to celebrate with me. I spent approximately $800 on appetizers and a 2 hour open bar. It was an event I’ll never forget.
I woke up the next day at 5am with a huge hangover. I couldn’t go back to sleep (obvious drunken morning sugar rush), so I decided to take a walk down to Fort Mason Park. When I arrived at the park I sat down and had an adult discussion with myself. It was time to make a change — a serious one this time.
The change was to let go of my 20’s and to let go of the toxic single life I was living once and for all. It was the first time I admitted to myself that I wanted a relationship.
Two months later my wish became a reality when my eventual girlfriend, Emyli, walked through my front door with a mutual friend of mine. We felt sparks right away.
30 Years Old: The End of My Single Days
For a myriad of reasons, it wasn’t easy courting Emyli. For one, when I met her she was conducting her 100 date experiment. Thankfully I was date #92 and on the tail end of her project.
Secondly, she had serious game — the type of game that would drive a grown man crazy. She was looking for a hunter, the type of man who would pursue her at all costs. Not once did she initiate a text conversation. She was subconsciously looking for chivalry, but probably didn’t know it at the time.
Lastly, she wasn’t afraid to friend-zone, test, withhold sex, or challenge me. If I met her a few years back, I wouldn’t have stood a chance becoming her boyfriend of 8 years. But at 30, with 5 years of big city dating under my belt, I stood out amongst her other suitors.
Long Term Relationship Snags
Emyli and I went on to have 8 years of incredible love for each other. I was her world, and she was mine. Currently we’re on an indefinite break as she works out some personal things on a 40 day vision quest out in Colorado and Wisconsin.
I won’t get into her personal business, but my vision is clear — she’s my soulmate and the one I’m supposed to be with. With that said, I’m no chump! You heard it here first.
You know what a chump is right? The type of man to persuade, beg, or plead a woman into getting back together with him.
Real men give their women space and time to work out their personal issues. They let things develop naturally and let the world do what it may.
Don’t get me wrong — I’m still supporting Emyli and I miss her. And I know she misses me.
Dating at 40 versus 30
So after 8 years of being in a relationship, I find myself pseudo-single again here in San Francisco.
Today I had a phone call with an old friend and colleague of mine named Terrance. We met around 13 years ago when we were both single and in our 20’s. We were exploring work, life, and of course women together for about 5 years.
He’s now 40 and I’m 38. In fact, he’s the friend of mine who introduced me to Emyli.
One of the things Terrance and I were discussing on the phone today included dating standards and dealbreakers. You see, when you get a bit older, you’ve likely had many relationships, girlfriends, and dating partners. You’ve seen the good and the bad. You know what you like, and you know what you would never venture into again.
For example, today I would never try picking up women at bars and clubs. Why? Because I don’t want a hangover or my next girlfriend to have drinking problems.
Today, if I was to use a dating app to find a relationship, you better believe I’d set a filter to segment out women with kids. Why? Because I’m at the age where I can date younger women or women without kids. When I 25 though, dating a woman with kids was just an experience.
If I went on a date at 38 versus 30 and learned the woman didn’t have a job or any career goals, I wouldn’t take her out for a second date. Why? Because I don’t need a dependent or new project. My hands are already full. When I was 30, I could care less if a woman I was dating had a job or not.
And lastly, if tomorrow one of my friends set me up on a blind date with a woman who was lazy or negative — I wouldn’t see her again. Why? Because that’s not the type of lifestyle I’m currently accustomed to living.
Should I Loosen My Dating Standards at 40? Are They Too Strict?
As you can see above, my dating standards at 40 are much stricter than they were at 25 or 30. If Emyli and I don’t work out our issues, the questions stands — should I loosen my dating standards?
It’s a difficult question to answer. Let us discuss it.
The other day I was talking to another friend of mine. We’ll call her Sarah — a single 39 year old female living in the Bay Area. We were talking about online dating and she admitted she only goes on first dates with men who check all of her boxes. These boxes included being over 6′ tall, having a six figure salary, owning a home, no kids, etc.
Then I asked her a difficult question with the hopes she wasn’t going to get upset with me. That question was “If you don’t mind me asking, remind me how long have you been single?” She said 7 years.
Then it hit me- dating standards suck and they are are overrated.
To answer the question in the title of this article, if Emyli and I don’t work out our differences– yes I would loosen my dating standards. And it’s not because of the fear of being alone– I just don’t want to end up like Sarah.
Imagine if I kept my standards too tight and I was single for 7 years. I’d be a super jaded 45 year old guy looking for a used Porsche to up my appeal towards 27 year old women. That might be for you, but it’s not for me. I want to share my life with a woman, even if she doesn’t check every-single-one-of-my-boxes.
Choose a woman who feels right, not who checks all of your boxes.
One of the reasons I was able to have an 8 year relationship with Emyli was because it FELT right with her. We were like two peas in a pod. Conversations always flowed. Awkward silences were never an issue. We had dozens of commonalities that made a joint-life super easy.
Emyli once told me that if she saw me on a dating app before we met, she would have swiped left on me. I said, “Ouch, I know I’m not the most photogenic person!”
Look, the point is — dating isn’t about checkboxes or lists. It’s about the way you feel when you’re around a potential partner.
Here’s some tips to know when it feels right with a woman you’re dating:
- Did conversation flow easily?
- Did you both have a similar energy level?
- Was her body language open towards you?
- Was it easy to be around her?
- Did you miss her right after the date ended?
- Did you struggle not to text her between your first and second date?
- Did you tell all your friends how effortlessly things went with her while on the date?
I know what your next question is — “What if it feels right with a woman but I’m hung-up on my checklist?”
Look man, you’re 40. You might not want to admit it, but you’re carrying a lot of experience and possible baggage from your past relationships. It will be difficult for you to let go of all of this.
My recommendation is even if you meet a woman who doesn’t check all of your boxes — if she makes you feel good, keep going on dates with her. Why?
Because what are the chances that you’ll find another woman who feels so good? Or what are the chances of finding someone who flows on your wavelength? Or someone who fits into your life like two puzzle pieces becoming one?
I’m not saying you’ll never find someone who feels right again. That’s just silly. But what if it takes you 7, 10, or even 15 years to find that next person?
Whether you want to admit it or not, you’re getting older. You have baggage too. Time is ticking away my friend. The next time you find yourself with a woman who makes you feel special, don’t let her get away — even if she doesn’t every single one of your checkboxes.
Need More Guidance?
Dating at 40 versus 30 can be drastically different. If you’re recently single after a long term relationship my suggestion for you is to work with a guidance counselor or therapist to heal any pain you’re experiencing.
Once you’re ready to date, I’d recommend you shift from a therapist to a coach. I say this because coaches help you reach your goals and help keep you accountable. To learn more about our dating coaching and matchmaking services here at emlovz, click here to watch a free webinar.
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