The Paradox of Modern Dating and Romance
We live in the most sexually permissive era in human history. Dating apps put thousands of potential matches at your fingertips. Hookup culture is normalized. Social media makes it easier than ever to connect with new people.
So why has dating never been harder?
Dr. Robert Glover, a relationship therapist with 40 years of experience, shared a stunning statistic on the Modern Wisdom podcast: “For the first time since they started counting numbers, over 50% of men and women 35 and younger report not having been in a relationship for the last year.”
Despite all our technology, dating boot camps, and swipe-right apps, people aren’t actually getting into relationships. And according to Dr. Glover, young adults are having less sex than previous generations, despite having more apparent access.
Something is fundamentally broken. Here’s what’s actually happening—and how to navigate it.
The Abundance Paradox: Too Much Choice, Too Little Commitment
Dr. Glover identifies a cruel irony of modern dating: the same technology that promises unlimited options is actually preventing people from committing to anyone.
For Men:
“Our grandfathers maybe saw three beautiful women in their lifetime and didn’t see any of them naked,” Dr. Glover points out. “Guys can go see beautiful woman after beautiful woman without a lot of clothes on—not even just on porn, but just on their Instagram feed, TikTok, whatever.”
The result? Even when a man is with a desirable woman, he’s constantly thinking: “But she’s cuter, she’s cuter, she’s cuter.” This creates a paralysis: “I can’t make any kind of ongoing commitment to this one because there might be this cuter one that I want to be with.”
Dr. Glover is blunt with his clients: “Number one, of course you’re always going to see prettier, younger women. And the woman you’re with also sees the prettier, younger women and knows you’re thinking ‘wouldn’t it be nice.'”
His advice? “You have to stop that kind of ruminating—’I’m with this one but because I’m with her I can’t be with her.’ That serves no purpose. That will not move you forward in life. Because even if you weren’t with this one, you probably wouldn’t talk to that one anyway.”
For Women:
The dynamic is different but equally damaging. Dr. Glover believes social media provides women with a constant stream of attention, validation, and desire—”the feminine thrives on attention and desire and praise.”
“If I just commit to one guy, if I get all in with one guy, I’ve got to turn off my social media and this constant funnel of praise,” he explains. “I’ve got to quit putting sexy selfies of myself up and getting all the likes.”
The result? “We’ve got this technological world that makes it so easy to meet, connect, go fast, but actually getting together and staying together for any length of time” becomes nearly impossible.
The Fear Factor: Why Nobody Wants to Risk Anything
Beyond the abundance paradox, Dr. Glover identifies genuine fear as a major barrier to modern relationships.
For Men: The MeToo Concern
While acknowledging that the MeToo movement addressed real abuses, Dr. Glover recognizes its chilling effect on normal male-female interaction.
“I think for men, because men nowadays—even if we get a woman, maybe a woman that we consider desirable—we’re looking around, but what if we live in a world where if I just touch a woman’s arm, I don’t know if she’s going to have a major overreaction to that, or she’s going to go ballistic, or I become a hashtag MeToo casualty, or it goes on her social media?” he wonders.
When a young podcast guest asked what advice he’d give men his age (21), especially after the guest’s own experience of being falsely accused, Dr. Glover was remarkably honest: “I don’t know. I don’t know that if you have a fear that women are going to post anything and everything on social media and you’ve got no rebuttal and it’s going to be believed—you know, I don’t know.”
He notes the contradiction in the mantra “the victim is always to be believed”: “What if the victim is a man who’s been falsely accused? If he’s a man, he’s not to be believed.”
For Women: Physical Vulnerability
Dr. Glover acknowledges the other side: “I can understand as a woman, I’d put my guard up. I’d have my guard up if men were just approaching me in the gym and talking to me and I don’t know where this is headed, what they want, I don’t know them from Adam.”
The result? Both sexes are afraid to make moves, express interest, or take social risks. Everyone’s waiting for the other person to make it completely safe—which no one can do.
The Hookup Culture Myth
Despite the perception that everyone is hooking up constantly, Dr. Glover sees the opposite in his practice: young people are actually having less sex and fewer relationships than previous generations.
Why? Beyond fear and abundance paralysis, he identifies a more subtle issue: the confusion between casual sex and emotional connection.
“I think in women, when they open up to have sex with a man, they also tend to open their heart up and begin thinking in terms of the relational dynamic with this person,” he explains. “Not just ‘oh that felt good to have sex,’ but ‘I like being with him, I want to see him again, I want to know him, I want to connect.'”
Men, on the other hand, are more likely to compartmentalize: “Oh, if I can keep having sex with three or four women, why would I stop doing that?”
This creates inevitable mismatches, even when both parties explicitly agree to keep things casual. “Even when I told women up front, ‘I’m just recently out of a relationship,’ they’d go ‘great, great, great,'” Dr. Glover recalls. “I’d start seeing that look in their eye and I’d remind them again and they all would say the same thing: ‘I heard you the first time.'”
Their brain heard him. Their heart was getting connected.
How to Actually Navigate Modern Dating
Despite these challenges, Dr. Glover has practical strategies that work:
1. Become a Better Picker AND a Better Ender
When Dr. Glover re-entered the dating world in his late 40s after his second divorce, he realized: “I have to become a better picker and I have to become a better ender.”
Most people focus only on getting into relationships, not on getting out of wrong ones quickly. “Dating is making multiple bad picks, one bad pick after another,” he explains. “Go on a date and find out: do you want to go on a second date? If you don’t, end it right. You made a bad pick, but you didn’t know you made a bad pick until you went.”
Men tell him: “Robert, I don’t know what’s wrong with me. All my dates are just one and done.” His response? “Good. That’s how it’s supposed to work. Not every woman you meet should become your future wife.”
2. End Things Sooner Rather Than Later
Dr. Glover learned through painful experience that staying in mismatched relationships causes more harm than early, clean breaks.
“As soon as you realize a person is not somebody that you can’t imagine yourself not being with, it’s probably a good time to stop it,” he advises.
Even when the sex is good and you’ve been honest about not wanting exclusivity, if you see “that look in her eye” showing she’s developing deeper feelings you don’t share, “I would end it even if you’ve stated up front.”
Why? “I’d rather break her heart three or four weeks into it rather than three or four months into it. That does make a big difference.”
3. Live a Life Worth Joining
Rather than trying to convince someone to date you, build a life so compelling that the right people naturally want to be part of it.
After his divorce, Dr. Glover made a bucket list: “I want to learn to shoot a gun, I want to ski, I want to learn Spanish, I want to travel.” He took salsa lessons. He became what he calls “a social animal.”
“When I looked at women’s profiles with all the things they said they did—wine tasting, skiing, trips to Europe—I thought, ‘I want more of a life than that,'” he recalls. “The act of wanting to learn how to date drove me to start creating the kind of life I wanted to live.”
4. Practice Outcome Agnosticism
This is perhaps Dr. Glover’s most powerful concept: being “equally okay with every possible outcome.”
“What if you’re standing there, there’s a woman standing next to you, she’s reasonably attractive, and you want to say something to her? What if you were equally okay with every possible outcome?” he asks.
You might prefer some outcomes—of course you’d rather she respond positively than negatively—but what if you were genuinely okay with either?
“Attachment is the cause of all suffering,” he notes, quoting Buddha. “Attachment is also the cause of all anxiety. If you have fewer attachments, you might actually be more engaging and not so anxious.”
This doesn’t mean not caring. It means caring about living authentically more than controlling outcomes.
5. Say Yes to Life
One of Dr. Glover’s mentors told him: “It’s a sin to say no when you should have said yes.”
This became his guiding philosophy. “Most amazing things in my life have come from saying yes,” he reflects. “I say yes to interviews, yes to opportunities, yes to being part of retreats. I just keep saying yes, and it’s funny how things just keep coming to me.”
This includes saying yes to his wife. After getting massages from her for six months in Puerto Vallarta, she propositioned him. He said yes. “We’ve been married seven and a half years now. She is the most amazing, crazy beautiful, sexy woman I know.”
The Uncomfortable Truth About Social Media
Dr. Glover isn’t a fan of social media for relationships, and his reasoning is worth considering.
Beyond the comparison trap and the constant availability of “better options,” social media creates a false sense of connection that prevents real intimacy. It allows both men and women to get hits of validation and attention without the vulnerability of actual relationships.
“I’m not a big fan of social media for many reasons,” he says. “It has value, but I’m glad I’m not a young guy having to navigate it. It’s perilous.”
Can It Work? Yes—If You Do It Differently
Despite all these challenges, Dr. Glover maintains optimism. At 68, admittedly average-looking, having gone through bankruptcy, he continues to attract opportunities, friendships, and yes, female attention.
The secret? “There’s no magic to it. Get out of the house, expand your route, linger in public, talk to people, test for interest, walk through open doors, say yes. It makes you an interesting person.”
The modern dating landscape is harder in many ways than previous generations experienced. But it’s not impossible. It just requires rejecting the very approaches that technology and culture push on us: endless swiping, constant comparison, risk-free interaction, and commitment avoidance.
Real connection still happens the old-fashioned way: living a life worth living, being genuinely social, taking real risks, and being willing to both pick well and end quickly when something isn’t right.
As Dr. Glover puts it: “I love waking up in the morning not knowing how my day is going to end. I’ve had so many days getting ready for bed going ‘I did not see this coming when I got up this morning.'”
That’s not just a dating strategy. That’s a life strategy.