The Modern Dating Struggle—And How to Navigate It
If you ask any single person how their dating life is going, you’re likely to get an earful. It’s not just the frustration with dating apps, the exhaustion of cycling through mutual friends, or the overwhelming negativity surrounding the dating experience. It’s something simpler: dating is just hard.
Yes, factors like social media, the rising cost of living, and the increasing number of emotionally unavailable partners may amplify the challenge. But at its core, dating has always been about emotional investment, vulnerability, and the fear of heartbreak. No matter how confident we are in our careers or friendships, dating has a way of exposing our deepest insecurities.
Thankfully, podcaster and author Elizabeth Day, along with dating coach Mel Schilling (of Married at First Sight fame), are here to help. Their new podcast, How to Date, explores the modern dating landscape, offering insights on everything from navigating apps to making meaningful real-life connections.
We spoke with Day and Schilling about common dating pitfalls and how to avoid them in 2025. Take note and date smarter this Valentine’s Day.
1. Creating a Fantasy Before Reality
“As a writer, I had a bad habit of taking the smallest bit of information—like matching with someone on an app—and spinning it into a full-blown love story in my head,” says Day. “I’d imagine walking down the aisle, rose petals flying, all before even meeting them in real life. I had to learn to stop Googling people before dates to keep myself grounded in reality.”
2. Being Too Hard on Yourself
“Self-compassion is key,” says Schilling. “Dating naturally involves ups and downs, and rejection is part of the process. What matters is how you bounce back.” Instead of spiraling after a bad date, view each experience as a learning opportunity. “Every misstep teaches you something valuable about what you do—or don’t—want in a partner,” she adds. “Make sure your internal dialogue about dating is, at the very least, neutral. If it’s negative, reframe it.”
3. Sticking to the Same Type
“I kept going for the same kind of person—creative, artsy, but often unreliable,” says Day, who married in 2021. “Eventually, I realized I needed to shift my perspective. My husband is creative and loves the arts, but he also has his life together. I wouldn’t have met him if I hadn’t changed my approach.”
Being open-minded is essential. “I had a rigid idea of who I was looking for, and if someone didn’t fit that mold, I’d dismiss them. But dating—especially as you get older—humbles you. It teaches you that sometimes, your checklist isn’t what actually matters.”
4. Dating Without Clear Intentions
“What do you really want? A long-term relationship? Something casual? A long-distance connection?” asks Schilling. “Many people end up in situationships when they actually crave a committed relationship. Their actions—using hookup apps, keeping conversations shallow, frequenting places known for short-term flings—don’t align with their deeper desires. It’s like wanting to run a marathon but training by jumping hurdles.”
5. Ignoring Your Own Needs
“Mel and I talk a lot about ‘dating yourself’ first,” says Day. “For a long time, I didn’t truly know what I wanted. Many women, in particular, are raised to be agreeable, kind, and accommodating—qualities that can lead to people-pleasing in relationships.”
Day recalls a pivotal moment before meeting her husband. She had planned to move to LA and asked his opinion. “He said, ‘That’s tricky for you. I can’t make that decision for you.’ It blew me away. I was used to people either avoiding commitment or making dramatic declarations of love. His response forced me to reflect on what I truly wanted.”
6. Dismissing People Too Quickly
Modern dating fosters a culture of disposability, with endless swiping making it easy to assume there’s always someone better out there. “This mindset stops people from giving dates a real chance,” says Schilling. “Slowing down and taking the time to truly engage with someone might lead to something incredible.”
7. Overanalyzing Text Conversations
“When I was single, I thought I was playing it cool while texting a guy who was upfront about not being ready for commitment,” recalls Day. “But looking back, I realized I was sending long, overthought messages while he responded with one-liners. I thought I was being witty and casual, but in reality, I was overinvested.”
8. Using Dating Apps the Wrong Way
Dating apps can work—Day met her husband on Hinge. But Schilling emphasizes the importance of using them wisely:
- Avoid using the same photos as your social media accounts to maintain some privacy.
- Don’t chat for more than two weeks before meeting in person—this reduces the risk of scams and helps manage expectations.
- Keep your profile positive. Instead of listing what you don’t want (“No single parents”), highlight what you’re looking for (“Excited to meet fellow book lovers!”).
9. Settling for Inconsistency
It’s easy to make excuses for flaky behavior when you’re into someone. “When I met my husband, he was a consistent communicator,” says Day. “He checked in daily, followed through on plans, and was reliable from the start. I had been so used to emotionally unavailable partners that at first, it felt strange—but it was actually just healthy and normal.”
Final Thoughts
Dating today may come with unique challenges, but the fundamentals remain the same: know what you want, be open-minded, and don’t settle for less than you deserve. Whether you’re navigating apps, meeting people in real life, or reassessing your own patterns, remember—every experience is a step toward finding the right match.
