Why Dating Is So Hard In Your 20s (From a Matchmaker)

I wonder how many rooms it would take to house every coming-of-age movie ever made. Collectively and unequivocally, we romanticize the tumultuous, yet beautiful stage between youth and adulthood. We’re repeatedly told that our 20s will be the best years of our lives, the one decade we have for self-discovery and adventure. However, that’s only a half-truth; being a 20-something is also filled with uncertainty, mistakes, and the gnawing question of, “Am I doing this right?”.  Sure, your 20s can be a ton of fun, and most of us catch a glimpse of the heart-pounding, head-spinning, rush of enlightenment and stupor often portrayed in the movies. But more often, being a 20-something is overwhelming, exhausting, and brimming with confusion. From finding a career path, growing distant from longtime friends, and learning how to pay your electric bill, being in your 20s certainly isn’t the Hollywood dream that was sold to us. But I’m still leaving out the biggest elephant in the room: dating.  Dating is both a blessing and a curse in your 20s; when its good, it’s great, but more commonly, it’s like walking blindfolded through a battlefield. You don’t have the same life and relationship experience as a fully fledged adult, but you have the new-found freedom to explore and learn. There will be plenty of love, romance, and sexual awakenings in your 20s, but with that comes the opposite: heartbreak and loss. I know that’s quite a gloomy outlook, but it’s the reality. If you’re in this season of life feeling the full weight of uncertainty and struggle in romance, you’re not alone. I’ve been a Matchmaker and dating coach for over 2 decades, and most of my 20-something clients come to me frustrated and burnt out of the dating scene. Trust me, I deeply understand why dating is so hard in your 20s; I’ve been there and done that. Having came out on the other side of my 20s, I know a thing or two about what to do and not to do to thrive in the dating scene, and how to navigate dating in your 20s with grace and self-compassion.  

Why Is Dating So Hard In Your 20s?

1. No Romantic Experience

For most of us, our 20s are when we venture into our first “real” relationships. Sure, you probably had a high school sweetheart or had your first kiss. Maybe you even had some risqué, NSFW fun on prom night. But adult relationships are an entirely different ballgame for men and women alike. For the first time in your romantic life, you need more than lust and desire to make a relationship work. Now, communication skills, emotional maturity and availability, and boundaries are more important than ever before. There’s just one issue: you’re likely still learning all of these skills, which means you’re navigating these nuances without much know-how. Let’s take one of my more recent clients as an example. Sara had just turned 23 when she started receiving a very substantial trust from her grandfather. She was young, beautiful, and suddenly more wealthy than her own parents. She truly was the total package, at least, from the outside looking in. She had almost everything, with just one variable to solve: a life partner. She joined my Matchmaking service intending to find the one immediately; after all, she really was a desirable partner, and she knew it. There was just one issue: she didn’t know how to actually be a good partner. She often failed to see other peoples’ points of view and approached life as if it’s some game to be won. From the surface, Sara seemed unforgivably shallow and cold-hearted, so much so that I almost turned her down as a client. However, I soon realized that her superficiality was really just that; she cloaked herself in ego to hide her very vulnerable, sensitive, and empathic id. Pulling back layer by layer, I soon saw that she was a good person underneath her mask. She was just terrified of being hurt. Together, we worked on building real confidence and throwing away the artificial mask she donned. She learned how to be genuinely vulnerable and express her needs openly, even at this risk of sounding needy. She finally understood how to push beyond the fear and communicate her real self. Only after months of date coaching did I start her match search, and she’s still happily in love with one of her matches. Her journey taught me that the uncertainty of inexperience can be both humbling and empowering; it’s a chance to learn what you truly want and need from a partner.  

2. Casual Flings and Situationships

As someone who spends their life curating deep, meaningful relationships, I don’t understand the appeal of hookup culture. It’s a near unescapable circumstance of dating in your 20s, and is often a real obstacle for anyone trying to find a lasting partnership. Casual flings and situationships are murky, undefined, and usually have more strings attached than either party openly admits. Still, they dominate the dating landscape for all age groups, especially 20-somethings. The irony is that most people don’t actually want casual relationships; they more or less incidentally end up in them. What they truly crave is connection, but hookup culture has made commitment seem like some taboo or forbidden subject, and it’s incredibly difficult to get anyone to commit. I once worked with a client, Jake, who found himself caught in one situationship after another. He wanted something real and meaningful, but felt pressured to be aloof and play it cool. More than he wanted commitment, he wanted to not be ostracized from his friend group who were still sowing wild oats. In a dating scene that emphasizes casual flings over depth and loyalty, it’s hard to be like Jake, caught in the middle of expectation and desire. My advice to him, and to you, is this: don’t settle for less than what you want. There’s nothing wrong with hookup culture if that’s what you’re truly seeking, but don’t simply fall in in line with the crowd because that’s what everyone else is doing. I can’t pretend that it’s easy to find a real, lasting relationship; hookups and flings are the standard for 20-somethings. Relationships with love and commitment are rare, but if that’s what you truly seek, stand firm on your intentions and don’t cave to the social pressures. After a few months of coaching, it clicked for Jake that having a life partner was more important to him than fitting in, and I was able to match him with a wonderful young lady with the same values.  

3. Instability and Uncertainty

As I mentioned, your 20s are a time of immense growth, exploration, and change. One day, you’re certain that you want to sell everything you own, buy a van, and life an adventurous nomad life. The next, you’re dreaming of stability, family, and a white picket fence. The world is your oyster, and you know it, which means actually deciding which path to take can be overwhelming. You don’t even really know what the future holds, how can you expect to feel fully aligned with someone else’s vision for the future? Emily, one of my clients, wrestled with this for years. She was torn between a high-powered career in graphic design and moving to the Colorado mountains to start a farm. She’d casually dated before joining my services, but she hit a roadblock every time her goals shifted. The truth is, dating while you’re still figuring it all out is tricky. It’s like trying to hit a moving target; it’s possible, but you need luck on your side. Here’s the silver lining: this is the best time to experiment and explore! Your 20s are your last decade where uncertainty is acceptable, so embrace it. You don’t need to have a clear, rigid definition for your future… yet. What actually matters is that you stay true to your core values, the guiding principles that won’t change, no matter how much your life evolves. Aspects of your personality like morals and values are what truly define compatibility and set the tone for all of your relationships. Fortunately, Emily’s journey ended on a high note, with her taking the path less traveled. She eventually decided to settle in Colorado, and I helped her find a hiking and farm-loving mountain man who was ready to help her build her dream life.  

4. Financial Stress

Let’s face it: most people in their 20s aren’t swimming in cash. Between student loans, rent, and entry-level salaries, it’s hard to budget for groceries, let alone expensive dinners or romantic weekend getaways. But here’s the secret that the restaurant industry keeps tightly: dating doesn’t have to cost a fortune or involve Michelin-starred restaurants. Really, the best dates are usually the simplest ones. Think sunset picnics, spending the day at a street fair, or cozy date night at home in with a warm dinner. The key is that any good date should be thoughtful, intentional, and relate to you and your love’s interests and hobbies. As I write this, I’m reminded of Alex, one of my past clients who was embarrassed about his tight budget. I know you’re wondering how someone without a ton of free cash joined a luxury Matchmaking service. One of Alex’s strongest qualities was his ability to save, invest, and stretch his wallet. He saved for a year to join my service, despite being worried that his financial situation would make him less appealing to potential matches. I told him that the right person would see all of his other amazing qualities and realize that although he wasn’t wealthy right now, he had the chops to provide stability to a partner down the road. Alex really struggled to overcome his financial anxiety with dating, but he slowly inched towards acceptance. After a few months of coaching, everything we’d been building fell into place; it finally clicked for him that effort, intention, and potential was infinitely more attractive than a ton of money. My hope for you is that you achieve the same epiphany as Alex and realize that almost everyone in your age group is in the same financial position. Other 20-somethings aren’t expecting generous wealth just yet; they want a partner with real potential. Instead of fixating on what you don’t have, focus on building your future day by day. Until you’re more financially secure, any potential partner worth your time will be perfectly happy spending time with you, no matter the venue.  

Why Matchmaking Can Help

People often equate Matchmaking services with middle-aged singles looking for a second chance at love. Surprisingly, many of my clients are 20-somethings! Most of my 20-something clients join LUMA because they’re tired of the burn-and-churn cycle of hookup culture, but don’t know where to even begin finding a loving, lasting relationship. They know they want something real, but don’t have a clue where to find it. Matchmakers help 20-somethings navigate the chaos of modern dating with personalized guidance and support, no dating apps or algorithms involved! Whether it’s through one-on-one coaching, highly compatible matches, or concierge services like date planning and wardrobe consults, matchmakers offer a way to cut through the noise and focus on what really matters: connection. Dating in your 20s is messy and imperfect, but it’s also a time of incredible growth and adventure. Embrace the lessons, trust the process, and remember that you don’t have to figure it all out alone. If you’re ready for dating to be easy and fun, talk to us about our membership options.