A relationship expert's number one tip for dating in every decade
Lifestyle
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2:00 PM on Wednesday, June 18
By Erica Garza for Hims, Stacker
A relationship expert's number one tip for dating in every decade
Aging has certain advantages when it comes to dating. You’ve got life experience and a pretty good idea of what you want and don’t want in a partner — and you’re a lot less likely to waste time on playing games.
But let’s be real: Today's dating scene isn’t what it used to be. Between needing to learn to navigate swiping, ghosting, breadcrumbing, and more, it’s basically a whole new playbook.
So, how do you date and pursue a potentially sexual relationship confidently when the rules are always changing? Hims asked Debra Castaldo, PhD, LCSW, MS, a relationship expert, therapist, and author of “The Return to Love Playbook,” who publicly goes by “Dr. Deb,” to share her best advice for men in their twenties and beyond.
Keep reading to get her top tip for each decade — and learn how to navigate modern dating on your own terms, no matter your current chapter of life.
Dating in Your 20s: Define Your Values
Although many equate the twenties with adventure, exploration, and impulsiveness, Dr. Castaldo encourages young men to slow down and define the values they want to live by.
While experimentation can help you figure out what you like and don’t like as you step into adulthood, there may come a time when you want more than just an empty hookup. “I have treated young men in my psychotherapy practice who have grown weary of the college hook-up scene and begin to find it unfulfilling to have different partners every week,” says Dr. Castaldo. “If you are stuck in a pattern of one-night-stands, ask yourself if this behavior is serving you and what the consequences may be not only for you, but for your partners.”
She says this decade is also an important time to adopt healthy habits towards sex. Checking in with yourself and your partner to ensure you both feel emotionally and physically safe is crucial. You should also be willing to have “courageous conversations” about consent, protection, and regular STI testing.
If you don’t feel willing to have these conversations with your partner, you may not be a good match, warns Castaldo. “Being completely transparent and willing to share intimate thoughts and feelings is the foundation of a healthy attachment, and is part of the foundation of a good relationship.”
Dating in Your 30s: Lead With Intention, But Don’t Rush
There’s a shift that often happens when you’re dating in your thirties: You’re not just chasing the adrenaline of attraction. Rather, you may be prioritizing compatibility and shared values.
But that doesn’t mean you have to have it all figured out. “There is often tremendous pressure to settle down with marriage and family,” says Dr. Castaldo of dating in this decade. “I encourage you to take your time and ask yourself some big questions instead. What’s your vision for life? How do you need to grow as a potential partner?”
You may also benefit from taking the time to figure out what qualities you want in a partner to help you get to know the person sitting across from you at that first dinner date. But also, be realistic and patient in your expectations. “In my opinion, it takes at least a year to get to know the real person and what a full-time committed relationship would be like with them,” says Dr. Castaldo.
And regarding sex, Dr. Castaldo suggests introspecting about what kind of partner you want to be in your thirties. “This decade is a great time to shift from the focus on desire and lust we often have in our twenties to a more mature approach of being a partner who gives pleasure.”
Dating in Your 40s: Get Clear On What You Want — And Own It
The smartest move you can make when dating in your forties is to be upfront about what you want. Whether you want to keep things casual for a while or secure a long-term partner, clarity helps you avoid mismatches and wasted time.
“These days, marriage and family are often delayed, with many folks choosing to remain single, or in a relationship but not living together,” says Dr. Castaldo. “If this is your goal, be honest about it so you are not creating false hope with someone who wants commitment or marriage.” The same guidance of prioritizing honesty also applies if you are seeking a committed long-term relationship or marriage. Dr. Castaldo recommends making your intentions known early on, no matter where you land.
Your forties can also be a decade of embracing confidence. With a better understanding of who you are and what you want, you can avoid looking for someone to complete you. “Most people want a partner who also has a mature sense of themselves and wants a relationship that will add to their life, not a ‘half’ to fill up their own ‘empty half.’”
Having a better understanding of who you are also means understanding what parts of you could use some attention and care. “The forties are also a time when many find they repeat the same relationship mistakes over and over,” says Dr. Castaldo. “Now is a good time to work on those patterns to break the destructive cycles of unhealthy relationships.”
She recommends folks dating in their forties to pursue individual psychotherapy or couples therapy with a mental health professional to explore their relationship history and become consciously aware of who they’re attracting.
Dating in Your 50s: Don’t Stress, Reflect
When dating in your fifties, it’s not unusual to worry about how much time is left. But this kind of panic can lead you to act out destructively in an effort to hold on to your youth.
Dr. Castaldo offers an alternative possibility. “Use this time as a period of life review rather than crisis. By this time, you may have had many loves and even multiple marriages. Let your experience define your vision for going forward.”
She also suggests rethinking what it means to be in a mature partnership with someone. “Long-term relationships are most successful when there is good companionship and friendship, strong communication skills, the ability to tolerate and value differences, and consistent effort in keeping your sex life vibrant and growing.” Dr. Castaldo adds that dating should be a path to discerning who may or may not have the qualities that mean the most to you at this time in your life.
Dating in Your 60s and Beyond: Let Experience Guide You, Not Limit You
Dating in your sixties allows you to tap into your decades of wisdom and use your life experience to guide your choices.
“I find many folks give up in this decade, and either isolate themselves due to past hurts, or repeat the same mistakes,” says Dr. Castaldo, who instead suggests folks “rely on your ability to ‘know thyself’ and be transparent about who you are. One of the greatest obstacles in relationships at this age is inauthenticity.”
While most dating books will caution you against oversharing on your first date, being upfront about who you are early can fast-track you to the right relationship. “I am in favor of sharing who you are and what your relationship experiences have been as quickly as possible when dating at every age,” says Dr. Castaldo. But she says it’s essential in your sixties when time is of the essence.
You also shouldn’t buy into the myth that sex gets less important as you age. You can and should still lead a fulfilling sex life as you get older, but you may need support, whether that’s through medication, therapy, or lifestyle changes. “Yes, it may take more effort to wake up your sexuality, but focusing on giving pleasure to your partner, rather than expecting desire to magically appear, usually keeps the flames burning.”
In other words, intimacy takes work, but that’s true for any decade.
The Bottom Line: Your Best Relationship Starts Now
No matter how old you are, the best dating advice is timeless: Be yourself, be honest about what you want, and stay open to growth. Each decade may present new challenges, but it can also bring new opportunities to connect with someone more meaningfully from a place of deeper self-awareness.
This story was produced by Hims and reviewed and distributed by Stacker.
