Men: It’s Time to Rethink Your Dating Approach — This Expert Can Help You Attract the Partner You Really Want

The Short Version: Dating coach Kimberly Hill specializes in helping men rebuild confidence and find meaningful relationships after divorce or long-term relationships. With years of experience and certifications in neurolinguistics and solution-focused coaching, Kimberly has helped more than 350 men overcome dating app fatigue, break old patterns, and develop a fresh, self-reflective approach to dating. 

My parents’ divorce had been brewing for so long that it took my father more than five years to even think about reentering the dating scene. He wasn’t heartbroken — both he and my mother seemed much happier — but I couldn’t help but feel that loneliness still lingered around him.

When I finally asked if he’d ever date again, I expected him to laugh it off, maybe joke about his crush on the waitress at our favorite pizza place. Instead, he simply said, “I’m not ready yet.” 

At the time, I couldn’t fully grasp what he meant — the hesitation, the unspoken weight of starting over. It wasn’t until adulthood that I realized that dating after divorce isn’t just about finding someone new; it’s also about putting yourself back out there — which often includes rebuilding yourself in the process.

But that’s exactly the kind of journey that dating coach Kimberly Hill specializes in: helping men rebuild confidence, break unhealthy habits, and find meaningful relationships after a breakup. 

“Men, particularly in dating, are often an underserved group. When I started five years ago, there weren’t many women coaches working with men on relationships,” Kimberly noted. “Over time, I’ve worked with so many men that I really understand the themes and challenges they face, and I can offer that female perspective.”

I love this — it’s as they say: Having more than one perspective can make all the difference. And, who knows? It may have made my father’s journey a lot easier, too.

Kimberly’s life experience likely surpasses what most of us would imagine. 

She left her hometown of Vancouver and bought a one-way ticket to Bangkok and never looked back. Over the next decade, she lived in Sydney and Singapore, launching a career in finance with one of the world’s largest inter-dealer brokers.

Funny enough, it was in Australia where she started her journey toward coaching.

“I worked on a trading floor with 98 men. Many became good friends, and I often saw how they struggled to balance career with marriage or dating,” Kimberly recalled. “I realized I had a unique perspective on what the men around me were going through emotionally.” 

During this time, Kimberly was working with her own coach — someone she spoke to regularly who helped her navigate life, love, and the challenges of being a young professional in her 20s.

It was there that Kimberly had her “aha” moment: She wanted to help people like she’d been helped. 

“I’ve come to believe that we often teach what we need the most, and I needed this kind of support,” said Kimberly. “It turned into what I do today. And since I’d always worked with men, it felt natural to continue doing so.”

She earned certifications in neurolinguistics and solution-focused coaching and was named a Top 10 Dating Expert of 2023. Kimberly specializes in helping men build self-awareness and set realistic expectations with a clear vision to move forward.

You may have noticed I haven’t yet addressed the elephant in the room: dating apps.

I think dating apps are a hassle for just about everyone. I’m grateful to have met my partner before they became popular — hearing my single friends’ experiences has been more than enough to turn me off.

Kimberly’s clients often feel the same way. Typically, they are successful men reentering the dating world after a divorce or long-term relationship, looking for something deeper than the swipe-and-scroll of dating apps.

“They’re often baffled by dating apps and the whole process. Their challenges are different from a guy in his early 20s just starting out,” Kimberly said.

She makes a great point. Rewind 15 years, and dating looked completely different — no swiping, no instant messaging. Instead, it was mostly dating sites where you were lucky to get a response within a week. 

Fast forward to today, and courting has become a fast-paced game of reading through text and swiping through people like you’re browsing a takeout menu. 

“I noticed when men dip their toe back into the dating pool, they’re often thinking, ‘This is not what I remember,’” Kimberly explained. “Expectations in dating have drastically changed, and so many men I work with just find dating to be frustrating now.” 

The rules have definitely changed, but so has the pressure to keep up. One of the most common things Kimberly hears from men is their apprehensiveness toward dating apps and texting. 

“A common sentiment I hear is, ‘If I could just get on the date, they’d see who I really am.’ It’s everything leading up to that date — the match, the first message, the texting — that brings up a lot of stress and anxiety,” she said.

So Kimberly works with men all the way up to the date: the match, the first message, the conversation, when to ask a match out, and how to keep things feeling exciting through phone calls or text messages.

“It’s often about a mindset shift — adjusting your perspective and expectations. Once men get that shift, they can actually start having fun with it, enjoy the experience more, and really embrace dating for what it is,” Kimberly added.

With that in mind, Kimberly offers three types of services: 

• Online Course: An online course version of Kimberly’s private coaching will be available at the end of 2024. It’s designed for men who prefer to work at their own pace. 
• Masterclass: In less than an hour, learn directly from Kimberly in her Masterclass to learn the “10 Must-Know Tips for Communicating With and Understanding Women.” 
• One-on-One Coaching: With private, one-on-one coaching, men can learn how to build their confidence, overcome destructive patterns, and start connecting with different types of people.

But learning to move from swiping on apps to real-life connections is only part of the journey. The other part? Well, let’s just say it involves a lot of self-discovery.

Anyone with anxiety knows how tough it is to live in the moment. There’s always that endless to-do list running through your mind or the pressure of unrealistic expectations about where you’re “supposed” to be. 

But life isn’t meant to work that way.

This is something Kimberly often has to remind her clients. She says it’s not uncommon for men to feel confused and burnt out after a series of bad dates or mismatched conversations. 

“If they don’t attract the right kind of partner, it can impact their confidence and bring in feelings of shame and guilt,” she explained. 

That’s when the self-discovery work begins. 

Kimberly starts by exploring patterns, helping men identify whether they’re trying new approaches or just falling back into the same habits. She describes this as a “pretty involved exercise that takes a few sessions,” but the outcome is worth it.

“From there, we reverse-engineer to identify the small, nuanced changes needed for a new kind of experience,” Kimberly said. “Ultimately, it’s about unpacking what’s really going on and making shifts, so you’re attracting a different kind of person.”

Kimberly is doing cognitive behavioral therapy, and her clients often don’t even realize it.

When we talk about “attracting a different kind of person,” we’re not talking about unrealistic expectations, like dating celebrities or flawless models. It’s about breaking patterns that keep leading to the wrong type of relationship.

I have a friend who notoriously chooses the “wrong” person. He wants a stable, monogamous relationship, but he keeps dating emotionally unavailable women. It’s happened so often that it’s become a running joke in our friend group — but we all know he’s stuck in a cycle that keeps him from the kind of relationship he really wants.

Kimberly’s mission is to help men break out of those kinds of self-sabotaging cycles. For many men, especially after a divorce, self-esteem can hit an all-time low. But it’s important to learn to overcome that.

Kimberly compares this mindset to golf. Yes, golf.

She put it this way: If you shank your first shot and immediately think, “This is going to be a terrible day,” that single thought shifts your entire mindset. But if you shrug it off as a minor hiccup, you’ll probably find that the day isn’t so bad after all. 

Call it the modern-day manifestation. 

“It’s really similar to dating: Sometimes, you have a rough experience, like a bad date or a tough breakup, and you let that one thing taint the whole process,” Kimberly explained. 

Along with a positive attitude, Kimberly emphasized the importance of understanding that men and women communicate differently. And no, it’s not a throwback to outdated stereotypes or a concept from “Men Are from Mars, Women Are from Venus” — there’s real truth to it.

“Men and women approach dating differently, with slightly different communication styles. So, for men, if you’re approaching dating in a strictly logical way, you’re probably not going to get the experience you’re hoping for,” Kimberly said, then laughed: “My unconventional advice? Stop trying to be so logical.”

It’s not a bad piece of advice to end on. But there’s more to lasting change than just a shift in mindset. 

Rediscovering yourself and practicing self-reflection is not easy. It can bring up hidden pain and hard truths you probably have buried for years. But most of us know that growth comes from facing those hard parts of ourselves.

All you have to do is take that first step. You can schedule a free dating strategy call with Kimberly on her website.