Introducing Dating Maximalism
Why doing more for love means a more satisfying love life
When the stock market drops dramatically, my financial advisor tells me to “buy the dips.” His theory - borne out by the fact that the stock market has gone up by an average of 10% for 100 years - is that scared investors pull their money out, allowing brave investors to get in at a better price.
Fear, while often a protective mechanism, is also a poor coping strategy. The fear of risk causes you to think short-term instead of long-term. Whether you’re pulling your money out of a stumbling market or keeping your cash under the mattress, you’re missing out on extraordinary long-term gains. If you invested $100 in the S&P 500 in 1920, you would have $2,636,476.96 by 2023. If you held onto that $100, you could have dinner in 2023.
Yet, despite these eye-popping statistics, most people remain risk-averse. One can understand. If you’re living paycheck to paycheck, if you’re one hospitalization away from bankruptcy, if you’re eyeing retirement, risk aversion is a rational strategy. But what if you’re not? What if you’re somewhat secure and you’re still sitting on the sidelines?
Obviously, this is a question for a dating coach!
I have been helping smart, successful women find love since 2003. The vast majority are 35-65, have college educations, earn six figures, own their own homes, and travel internationally. They have best friends from elementary school. They’ve raised amazing high-functioning adult kids. They’ve achieved everything that they’ve ever wanted, except for one thing: they haven’t been able to create lasting love with a partner.
Maybe you can identify. Maybe you’ve given your heart to too many unworthy men over the years. Maybe you even got married once or twice. And what happened? He lied. He stopped making an effort. He cheated. He changed for the worse. He became verbally abusive. The man who was supposed to be your biggest fan became your worst nightmare. Every attempt to find a better man leads to the same outcome: a brief period of excitement, and the inevitable disappointment that it was all too good to be true.
Is it any surprise that relationships feel like the ultimate risk? That many women don’t want to take that risk? That there is a parallel between risk-aversion in investing and risk-aversion in dating? That, perhaps, having too much short-term fear may cause long-term damage?
Cheryl grew up in poverty. Dad was a drinker. Her parents lived in separate bedrooms. She thought getting married would be a great escape. Her husband was good-looking. He was educated. He represented security. What she didn’t know was that he was a religious zealot. Not only that, but he wasn’t sensitive to her emotional cues, he didn’t desire her physically, and he didn’t want to spend time with her. Nonetheless, Cheryl stayed with him for twenty years to be a positive influence on her daughters.
She joined Love U last year and while she’s made tremendous strides, Cheryl still reverts to her self-protective patterns, forged by her alcoholic Dad and her emotionally unavailable ex. She pulls away and keeps her guard up, to protect herself from bad men. It’s understandable but it prevents her from making meaningful connections when she meets good men.
Last week, Cheryl had a great first date with Adam. Unlike most men she meets, she was attracted to him. Despite that, she:
Shut down the conversation when asked about her past because her past isn’t something she’s proud of.
Left after two hours, figuring they would run out of things to say.
Refused to kiss him, even though she wanted to.
Perhaps you would have done the same. If that’s the case, I want you to consider the role fear has in your love life, and how it may unintentionally get in your way.
Cheryl believes that men are guilty until proven innocent, that if you let a man in, he will hurt you, and that it’s far safer to keep all men at arm’s length. If, indeed, all men were bad, that would be a wise strategy. But all men are not bad. Most of them are just as confused and frustrated as you are about dating. Instead of seeing men as normal human beings, Cheryl sees them as potential threats. Even on a date where she’s seen no red flags, like the one with Adam, she’s still subconsciously pulling away to protect herself.
Imagine a slightly different Cheryl making slightly different choices:
Instead of saying she has to leave after two hours, Cheryl joins Adam after dinner for a few rounds of drinks at a bar up the street. They go deeper into their conversation and don’t leave the bar until the lights go on at 1 am.
Instead of shutting down his curiosity about her past, Cheryl acknowledges Adam’s desire to get to know her better, shares a bit about her bad marriage without delving into the details, and redirects the conversation back to him.
Instead of rejecting Adam when he made a move (which only leaves him feeling embarrassed or confused), Cheryl could have reciprocated his kiss and left him feeling excited about coming back for a second date.
We can both acknowledge Cheryl’s right to have fears about men and also point out that those fears stop her from making better connections.
So, what makes for a great connection with a stranger? Openness. Warmth. Excitement. Curiosity. Trust. This is what Dale Carnegie wrote about in “How to Win Friends and Influence People” in 1936.
It’s no less true today. People gravitate toward those who are open, warm, excited, curious, and trusting. If you ask Cheryl, point-blank, if she would use any of those words to describe herself, she’ll tell you: ABSOLUTELY NOT.
Her experiences in a dysfunctional family and a dysfunctional marriage have caused her to live in fear of being vulnerable, letting down her guard, and making a guy feel good. She carries this armor everywhere and doesn’t fully understand how impenetrable it is.
In trying to protect herself from bad guys, she also protects herself from the possibility of good guys who sincerely want to know and maybe even love her. If you treat a good guy like a potential threat, you’re going to have a decidedly different interaction than if you treat him like a trusted partner.
This is why I think most people struggle with dating - and I want to propose an alternative solution that may seem counterintuitive.
I call it Dating Maximalism. Before I explain it, let’s establish that most people become dating minimalists, which I’ll define as making the LEAST possible effort to ensure a positive dating experience.
You download a free dating app on your phone.
You post a few photos and 2-3 sentences about you.
You start swiping on potential partners based on this limited information.
You engage in high-volume casual texting with total strangers who have no investment in you (and are also casually texting dozens of strangers).
You observe these text conversations have no depth, fade out quickly, or last for weeks without any escalation.
You decide to meet for coffee as quickly as possible to see if there’s chemistry. Bonus: you can leave fast and he doesn’t have to spend money!
You give him less than an hour because you’re both so busy.
You talk about meaningless stuff to avoid being vulnerable or ask him pointed questions to ensure your values are aligned in the future.
You discover that meeting strangers for 3 blind dates a week leaves you feeling hopeless and despondent.
You keep doing this and complain about how much dating sucks.
Does that sound eerily accurate? Can you also see why it’s ineffective?
You conclude it would be cheaper to be on a free app than a paid dating site, even though more serious candidates are more likely to pay.
You conclude it would be smarter to text 20 guys than to have a few days of email conversation with a handful of men.
You conclude it would save time to meet a stranger for coffee, although it takes less time to meet that same stranger on FaceTime.
You conclude it would be more efficient to ask him what his intentions are than to treat him like an innocent man, without any agenda.
You conclude it would be safer to talk about your work and travels than to talk about feelings, hopes, and dreams, even though it doesn’t build intimacy.
You conclude it would be wiser to leave a great date early even though more time deepens your connection.
You conclude it would be foolish to reciprocate his advances even though it’s the very thing that cements him wanting to see you again.
I hope you can see that these are largely false conclusions that are hurting your chances of finding lasting love.
What’s Dating Maximalism?
It’s doing the opposite of the above, specifically because being a dating minimalist JUST DOESN’T WORK. It’s doing the opposite of what Cheryl does: looking for excuses to minimize interactions, treating every date as if he’s bound to hurt you, and sabotaging the chance for a real connection.
You use a paid dating site like Match or OKCupid on your laptop.
You take a few weeks to craft a compelling dating profile, detailing who you are and what you’re looking for, to entice higher-quality men to have higher-quality conversations with you.
You engage in a few days of long-form conversation on the dating site before moving the conversation to email. If you’re on an app and the organic move is to text, you can at least make your texts longer.
You schedule a phone call or FaceTime when he asks to meet.
If that hour-long “phone date” goes well, you feel comfortable going out for dinner on a Saturday night with a guy who you’ve seen, who likes you, and who now has some skin in the game.
By going out with one pre-screened man on a real date each week, you:
Don’t get stuck in texting hell forever.
Have more rapport, excitement, and trust on your dates.
Are more likely to feel more comfortable in being yourself with him.
Are less likely to have a bad date or no chemistry since you already “met” on FaceTime.
Have spent enough time before the date to make a connection that can end with a kiss and the potential for a second date.
Yet everyone insists on dating minimalism: swiping right, complaining about dull text chains, going on quick coffee dates, and wondering why it’s so hard to find one decent person in your entire city.
Is there a downside to dating maximalism? Sure. Some complain that they get a little too excited after a week of flirting and are let down in real life. Fair enough. But would you rather have one dinner date a week with a promising prospect or three dates with men you’ve texted but never spoken to?
I was once a dating maximalist. My theory: every other guy is doing the least he can to make you happy; I’m going to do the MOST I can to make you happy.
I’m going to call you a week in advance.
I’m going to plan the date for a Saturday night.
I’m going to offer to pick you up if you’re comfortable.
I’m going to choose a cool, atmospheric restaurant near your home.
I’m going to ask you questions about yourself and listen to your answers.
I’m going to order drinks, appetizers, entrees, and desserts.
I’m going to pick up the check, in full, no questions asked.
I’m going to know of another place we can go for drinks afterward.
I’m going to walk you to your car or drive you home.
I’m going to kiss you goodnight if I get the sense you’re receptive.
I’m going to follow up the next day to ask you out again.
Do you have many dates like that? If you’re a dating minimalist, probably not.
You’re not “wrong” for trying to protect yourself from bad dates, but in doing so, you’ve largely precluded the possibility of having a first date like the one I described above. Amazing dates can’t happen if both you and the men you meet online are committed to doing less. LESS conversation, LESS effort, LESS time, LESS warmth, LESS trust, LESS flirtation. LESS follow-up.
Isn’t it clear at this point that less ISN’T more?
LESS conversation, LESS effort, LESS time, LESS warmth, LESS trust, LESS flirtation. LESS follow-up.
Isn’t it clear at this point that less ISN’T more?
I acknowledge that risk aversion makes a certain amount of sense - if there is evidence of risk. If you put all your money into NFTs and lost it, you may never want to invest in anything ever again. That would be a mistake. Instead of trying your hand in crypto or attempting to pick individual stocks, you can put your money in a diversified index fund. Voila. Minimal risk. Huge rewards.
The same goes for dating. Risk is going out with a guy with a face tattoo. Risk is going out with a guy who says he never wants to commit. Risk is going out with a guy who can’t hold down a job, is battling alcoholism, or has severe anger issues. While those things aren’t always apparent on a first date, you can easily cut off any guy who exhibits these red flags while you’re dating.
Thus, there is no risk in meeting a man you’ve talked to for a week, assuming he’s a decent person, being curious about him, and trying to make a real human connection, if only for one night. The only risk is the one not taken.
Put your fear aside, put in more effort before you meet, and embrace being a dating maximalist. You - and your future partner - won’t regret it.
Your thoughts, below, are greatly appreciated.
What I Got Wrong
From last week’s post, Is It Racist to Have Racial Preferences in Dating?
Just for some context, I'm speaking from my experience as a POC, but I don't speak for all POC.
As mentioned in the post, there's a difference between wanting to date someone of the same race/religion because you want that shared cultural experience vs wanting to date someone of the same race/religion because you look down upon others who are unlike you or whatever other ignorant trope. I think my issue with the conversation about interracial and interfaith relationships is that so many people are afraid to look at themselves in the mirror and question their biases - all of us have them. To combat any prejudice we need to start getting honest with ourselves.
Also I feel like my dating choices as a POC are way more scrutinized. No one ever asks my white friends why they only date other white people, just like how no one ever questions why white people generally only hang out with other white people. Why am I always the one questioned, when I'm the one that's open to dating guys of any race and religion?
With that said, I still try my best to not get too mad about it. I put in the work everyday to combat racism, unpack my biases, and surround myself with wonderful people that come from a variety of cultures, so I have no reason to feel insecure or defensive. I also love discussions around these topics, so I'm trying to be patient with (mainly white) people that are still coming around to digging deeper on these things.
Malaika
Link That Made Me Think
The Paradoxical Freedom of Tradwife TikTok by Kat Rosenfield.
Kat Rosenfield is one of my favorite cultural critics. A prolific writer and thinker with a wicked sense of humor and a moderate temperament, she is a woman after my own heart. In this piece, she does a deep dive into the social media phenomenon of women who… enjoy being housewives. These women are framed as anti-feminists and libertarians (and many are), but is there anything wrong with someone who chooses family over career? I may be a coach for smart, successful women but I approve of anything that makes you happy and doesn’t hurt anybody else.
On the Love U Podcast
I Was Wrong
After 20 years of coaching, 1000 blog posts, 300 podcasts, I was bound to make some mistakes. We're all human. We all have biases. We all have blind spots. On this episode, I'm going to share a few ways in which I've evolved over time and make a case for how it's important to know the rules before you make exceptions to the rules.
My Not-So-Viral Social Media Post of the Week
You Can Also See Me On…
Shaunie Sanders of Girl Take Note was kind enough to interview me. We discussed how to date successfully as a woman, the challenges women face in the dating pool, and how to navigate the modern dating landscape. We also talk about the impact of childhood trauma on dating and highlight the difference between therapy and coaching. Click on the link called How To Date Successfully as a Woman and lemme know what you think.
You HAVE to Check Out…
TV - The Old Man and the Pool - Mike Birbiglia is the best kind of comic - a storyteller who makes you laugh and leads with heart and vulnerability. If you are a Dad or had a Dad, this has even more resonance.
Movies - Fingernails - If you like weird, high-concept movies about love, like The Lobster or Palm Springs, this is for you. This one is about a genetic test that theoretically proves that you’re soulmates, and whether love is about similarity or compatibility. With its impressive cast (Riz Ahmed, Jeremy Allen White) and juicy premise, it’ll give you something to talk about after.
Books - The Promise of Sleep by William Dement - I was once an excellent sleeper. That changed about 7 years ago and this was the book I turned to when insomnia took over my life. Lots has been written about the subject but this guy is the go-to expert and this is the go-to book.
Substack - When It Comes to Sex, My Generation is Screwed by Rikki Schlott - You think it’s hard to date in your 50s? Try being in your 20s! Social media. Texting. Blurry gender roles. And, notably, the leftward political drift of women along with the rightward drift of men. I’ve never been so happy to be old.
The Honey Shot
Hi Evan. I am writing to give you yet another success story from your coaching. I started reading your blog back in 2010, and followed your advice religiously. It took a while (like 2 years!) but I finally started applying your advice to my dating life. I knew it was working when I was dating a guy who other women were chasing, yet he was pressing me for commitment. I didn’t think he was the one so I cut bait, but it was so EMPOWERING to be the one who made that choice vs the other way around.
After a string of lackluster online dates, I decided to put my love life on hold and focus on my career for a bit. On Memorial Day, I left the office on a holiday weekend and decided I’d try to swing by a friend’s barbeque on the way home. As soon as I got there, I noticed a tall, athletic, handsome guy that I’d never seen before. I sat next to him in the backyard and struck up a conversation. We got married on April 14, last Saturday.
I literally had to refer back to your material a few times in the relationship when my angst was getting the better of me, but I kept my anxieties in check. And even when I didn’t, he never wavered in his love and support. I’m so glad that I saw that his dedication to me was what made him the one for me, versus focusing on a few things that I didn’t like him about him as a way of pushing him away. Without your advice, I know that I would have messed this up. Right now, I’m on my honeymoon in the Maldives with the man of my dreams, thanks to your work.
THANK YOU THANK YOU THANK YOU for what you’re doing. Please know that you’re impacting women’s lives, even if they never sign up for your 1-on-1 coaching and you never interact with them. I’ve referred all of my friends to your work. And please don’t let anyone say your work isn’t feminist because you recognize the differences in how men and women are socialized and help women understand how and what men think. There’s nothing feminist about a woman being alone when she wants a male companion!
I’ve attached a photo from my wedding for you to see. And this is us:
Again, thank you for what you do. Please know that your true reward will come later. I know you’re not a super religious person, so take that as you will!
My very best,
Diana
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Good afternoon. This is a very good article and advice for people anxious about dating.