If you’re reading this blog, I bet you already know just how difficult dating in your 20s is. Society often romanticizes this season of life, but I think that’s because hindsight is 20-20. Sure, this is the time for self-discovery and exploration, but with that comes uncertainty. For most of us, our 20s are bittersweet, but I the bitterness comes from dating.
Your 20s is probably the last time in adulthood when your mistakes won’t derail your life. I’m sorry to be so gloomy, but it’s the truth. You probably don’t have a mortgage to pay yet and aren’t in a super demanding leadership position in your career. I’m guessing you don’t have a spouse or children, or you wouldn’t be on this website! My point is that you don’t carry the heaviest of life’s burdens yet, for better or for worse. With all of that freedom comes options, and sometimes, too many options. Trying to find a partner in your 20s can feel like finding a needle in a haystack because your peers aren’t looking for anything serious.
I spent half of my 20s in a career I loathed, and the other half bootstrapping a business, so I deeply understand how hard it is to date in your 20s. While you’re busy trying to figure out your life, everyone else is sowing wild oats. It can make finding a partner on the same page as you feel like a lost cause. These issues aside, there’s a reason why so many older folks think fondly of their 20s. Dating in your 20s can be rewarding if you stay true to your values and approach relationships with intention. In my guide, I’ll show go over the biggest roadblocks you’ll face dating in your 20s, and share my best tips for how to find love amidst the chaos and unpredictability.
Challenges of Dating in Your 20s
I wish I could give you one simple reason why learning how to start dating in your 20s is so challenging. Really, it’s a mix of inexperience and uncertainty, which I’ll dive into next, but first, I want to share my overall perspective. Navigating love in this season of your life is probably the hardest it will ever be. That should give you hope for the future, but I know it doesn’t solve the issues at hand. What I can promise you is that with time, your vision for life becomes clearer, and you’ll find who you are and who you’re supposed to be with.
No Prior Relationship Experience
By the time you’ve reached your 20s, you’ve probably had your first kiss or been on a movie date with someone. You might have even called someone your boyfriend or girlfriend. That said, teenage romances don’t count as real adult relationships. Adult relationships are deeply fulfilling, but are usually less passionate than teenage crushes. In your teens, you might like someone because they share your taste in music or because you think they’re cute. Creating a spark with someone special is admittedly easier in your 20s. Adult relationships are still based on mutual attraction, but they’re built on more solid foundation, like financial stability, dependability, loyalty, and communication.
I doubt that many people in their early 20s have shared a home, a pet, or a mortgage with partner, and these responsibilities add layers of nuance to relationships. The more responsibilities you share with a partner, the more important communication skills, setting and respecting boundaries, and fairly settling arguments are because there’s more hinging on the longevity of the relationship.
In your 20s, you probably don’t know how to build a solid foundation for a relationship because you’ve never done it before! You might not even know how to go about asking someone out without coming off creepy or desperate. Being inexperienced is something to be ashamed of; in many ways, it’s better to know nothing than to know the wrong information. I know the dating scene feels like a minefield for someone who doesn’t already know how to navigate it, but with time and more dating experience, relationships will start to feel more natural.
Hookup Culture and “Situationships”
Hookup culture is like a door-to-door salesperson; it shows uninvited, takes up a ton of your time, and you end up buying something you don’t like out of politeness. Seriously, hookup culture is so pervasive in the US that you don’t need to live in a major metropolitan area for it to be part of your local dating scene. In my experience as a dating coach and Matchmaker, I’ve found that most people don’t actually want casual flings! They’re just looking for real love in all the wrong places.
Hookup culture is so intrinsically tied to dating in your 20s, it’s nearly the standard. Situationships and one-off hookups are more normalized than committed partnerships for 20-somethings, which makes it incredibly difficult to find other singles in your age group who have the same relationship goals. Listen, if you are looking for hookups, no one is judging you! Now is the time for exploration, including in romance. But not every 20-something wants casual flings, and those that seek commitment and partnership are truly in the minority.
Peer pressure and social norms often convince 20-somethings to give into hookup culture, even if that’s not what they really want. This only further isolates relationship-minded singles from the dating scene, and often does more harm than good. If you’re a 20-something who wants a serious relationship, you have to stand your ground. Going against your values and crossing your own boundaries will never serve you in the long run. Over time, going with the flow of hookup culture when you don’t really want to is going to eat away at your self-esteem and make it harder to trust future partners. It’s better to be the black sheep than to end up becoming something that you don’t want to be.
Uncertainty About Goals and Values
Is there anything more polarizing than uncertainty? Some of us thrive in it while others drowned in it. Personally, I love uncertainty: it drives knowledge, understanding, growth, and transformation. There’s no greater time of uncertainty than your 20s: you’re probably still mapping out your career path, deciding where you’d like to live long-term, and figuring out your life-long hobbies, passions, and friends. You might not know who you are and what you want out of life. One day, you think you have it all figured out, but everything changes by the next. Having a lack of clarity and trajectory for your life means that you can’t be sure about much, let alone who your ideal partner is.
If you don’t know whether you want to get an RV and be a digital nomad or buy a house, get married, and have kids, there’s really no way you can find the right person for you. Until you zero in on the lifestyle you want, you’ll end up going through a lot of heartache in the dating scene. Uncertainly about your life goals is going to lead to mismatched expectations in relationships. When you first start seeing someone, you might think you two share similar visions for the future! But three months in, your mind may change, and now your goals are going to take you and your partner in opposite directions.
The worst part is that everyone has a different idea of what dating in your 20s should look like, which only adds to the uncertainty. Your parents might think it’s best if you settle down early and get married, while you friends are encouraging you to be more carefree. Your loved ones are probably pulling you in 1,000 different directions, and these conflicting opinions can make you feel even more confused about what you really want. My best advice? Don’t listen to opinions from people you don’t really respect, and take the time to really figure out what you want out of life before diving head first into the dating scene.
Financial Instability
For most people in their 20s, financial stability feels like a far-off dream rather than a near future. You know the stereotype: late nights at the office fueled by ramen noodles and instant coffee. Trust me, I get it! When I was in my 20s, I thought I had it all figured out as a corporate finance and process improvement consultant. Just a few years in, I realized my career wasn’t truly fulfilling, so I turned my finances upside down self-funded my Matchmaking company. So I know a thing or two about financial instability!
By your mid to late 20s, you’re probably still in early-level positions if you even have narrowed down your career. Low salaries paired with student loans, the insane cost of living, and simply affording groceries can make going on dates out of reach. It doesn’t help that the dating scene is superficial right now, either, and cares more about the cost of the date than the quality of the time you spent together. Not everyone is that callous, but society as a whole puts more emphasis on shallow luxuries than real connection.
With dating feeling more like a pay-to-play game than a journey to a lasting relationship, tons of 20-something singles are opting out of romance entirely. All of the recent statistics on marriages, birth rates, and dating trends show that people are settling down later in life, and the biggest reason is that life is expensive enough without a mortgage, spouse, and children. That said, dating in your 20s can still be fun and fulfilling, you just have to go out with the right people. Focus on attracting a partner who’s in a similar financial position as you or who doesn’t equate your wealth with your value as a person.
How to Start Dating in Your 20s
Dating in your 20s might feel like walking on eggshells, but shifting your mindset and incorporating these tips is going to make your experience much more fulfilling. Just about all of my 20-something clients joined my Matchmaking service with the wrong mindset about how find love, so don’t worry if you feel a little lost right now! I’ll help you find the balance between looking for love and staying true to yourself.
Be Clear on Your Intentions
Dating in your 20s is bound to be overwhelming if you aren’t sure what you want. Before you dive head first into the dating scene, decide what kind of relationship you’re even looking for. Are you ready for a serious, committed partnership, or do you just want to have casual flings? Once you do some soul-searching and find your answer, you should be upfront and honest with any love interests about your relationship goals. No one likes to be strung along, so treat others as you’d like to be treated! No matter what kind of connections you’re looking for, trust is the basis for any type of relationship. Being direct about your intentions is a win-win; you save time and energy, and the other person doesn’t end up with hurt feelings!
Stop Looking For Perfection
I recently had a 20-something client who wanted a woman who was ready to settle down and have children immediately, but was also hyper independent and had accrued her own wealth. Did you catch the irony? The truth is that “perfection” does not exist. There’s probably not a single person who ticks off all the boxes on your list, and that’s okay! What’s important is that you find someone who aligns with you on big-picture ideals, like your values, goals, and lifestyle. As for my previous client, I guided him through date coaching to help him determine what he really wanted from a partner before we started the match search. After some soul searching, it was clear that what he really wanted was a loving, nurturing partner, and he’s happily married to to a stay-at-home-mom to this day!
Don’t Rush Commitment
If you’re in your late 20s, I’m sure you’re already receiving a flood of wedding and baby shower invitations. Your friends mean well, but I know that watching everyone around you couple up and settle down can put pressure on your to do the same. I can promise you that love doesn’t adhere to a timeline; it doesn’t care that your friends are getting married, it will find you once you’re ready for it! If you’re a hopeless romantic and you love love, my best advice to you is to let relationships progress at their own pace instead of making the biggest dating mistakes. Rushing into a new relationships can make you blind to red flags, which causes more harm than good in the long run. Taking your time getting to know potential partners will give you a stronger foundation for the future than hurrying through the early stages of dating.
Set Boundaries Early
Nearly all of my 20-something clients have the same issue: they can’t set fair boundaries. Some people think that even the most reasonable boundaries will push potential partners away, and others are way too aggressive about it. There seems to be no happy medium for boundary setting. Having been a Matchmaker for over 2 decades, I can tell you that healthy boundaries are a non-negotiable in dating and relationships. They’re what separate healthy from toxic. You just have to approach any conversation about boundaries from a loving, empathic perspective. Plus, honing this skill is going to set you up for success in your career and other relationships, too!
Plan Affordable Dates
Dating in your 20s doesn’t have to break the bank! This season of your life is likely when you’ll have the least amount of pressure to take your date out to upscale lounges and 5-star restaurants. If you’re single in your 30s and 40s, that’s when you’ll really be expected to shell out hundreds of dollars for a date, so now’s the time to enjoy creative, low-cost date ideas. If you’re on a tight budget, try taking your love interest on a sunset picnic on the beach or at a park. This is so romantic, but also doesn’t require you to empty your wallet. If your date doesn’t like an intentionally planned, low-cost date, they weren’t the right one for you, anyway!
Shift Your Mindset For Dating
Dating is not some high-stakes game to be hastily won. Instead of adding pressure to your dating life and thinking every date has to be “the one”, have a little fun with it! One of my past clients really was the total catch; she was beautiful, successful, and emotionally mature. There was just one issue: she treated dates like job interviews. After her date with her first match, I met with her match to get his feelings on where the relationship would go. He told me that he liked her, but she made him feel like the success of their date was life or death. I helped her navigate her immediacy around relationships, and set them back up after some date coaching. The rest is history, and they’re still together today!
Stay True to Your Values
I had a client years back who had no trouble getting first dates, but was never asked on a second. I asked her why this could be happening, and she truly had no idea. I had her detail how her dates usually went, and I really couldn’t figure out why she kept getting ghosted, either, until she told me that she always caved in to pressure and got intimate on first dates. She said that she was looking for a long-term relationship, but her actions were telling another story. Compromising your values is tempting in our hookup-driven dating scene, but don’t fall for it! Anyone serious about getting serious isn’t going to ask for intimacy too early, so if your dates are turning sexual too quickly, this is a huge sign that you’re going out with people only looking for casual flings.
Learn How to Handle Rejection
Like it or not, rejection is a fact of life, and it’s something you’ll have to get used to in the dating scene. No one wants to be rejected, but the truth is that the more you put yourself out there, the more you’ll have to face being let down. That said, rejection isn’t usually a personal attack on your character or appearance! Think about it like this: over half of the US population is already in a relationship. Even if you’re objectively attractive, you’re still going to get rejected about 50% of the time! Just because you’re going to be rejected at some point isn’t an excuse to stop dating altogether, though. The more you try, the closer you get to success, and each stumble is an opportunity for personal growth.
Invest in Your Personal Growth
Here’s the thing no one tells you about dating in your 20s: you are your biggest limiting factor. In this season of your life, there are more open doors for you than there might ever be again. Once you reach your 30s and 40s, you’ll have less time to explore your personality and self-expand. Right now, you should be focusing on cultivating your passions, mastering your hobbies, developing your career, and making life-long friends just as much as you should be looking for love. Investing in yourself isn’t just going to help you build your dream life, it’ll help you attract your best possible partner. Plus, the more workshops, conferences, and social mixers you attend, the greater your chances are of meeting other singles like you!
Be Patient With Yourself
I’ve saved the best for last! Learning how to start dating in your 20s is a process of trial, error, and growth, and it’s crucial to be patient with yourself along the way. Not every connection is going to work out, and that’s okay! Sometimes, the rug will be pulled from underneath your feet. Life is a series of ups, downs, and everything in between, but you have to trust that what’s meant for you will find its way to you. Your life partner will find you exactly when they’re supposed to, and unfortunately, no sooner than that. All you can do is to keep moving forward and learn from each setback. Focus on progress, not perfection in dating, and even if it takes a while to meet your perfect match, you’ll still have fun on the journey.
Why 20-Somethings Choose Matchmakers
When people think of Matchmakers, they usually imagine that their clients are 40, 50, or even 60. Contrary to popular belief, about a third of my clients are 20-somethings! Most of my younger clients join my firm because they don’t even know where to begin looking for the right partner. They’re overwhelmed in the hookup-driven dating scene. They know they want commitment, but they don’t know where to find it. Matchmakers veer away from algorithms and casual flings; they hand-select each match and only take on clients who are looking for a serious, lasting relationship.
Matchmakers provide expert guidance and support for their younger clients with date coaching, post-date feedback sessions, and even wardrobe consultations. At LUMA, we have Matchmakers specifically trained to help 20-somethings find lasting love and committed partnerships. If you want a real relationship without the stress of modern dating, learn about our membership options today.
Dating Over 60: Expert Advice from a Matchmaker
