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Dating Habits Of 5 Generations

I have a friend who is a single male in his 40s. He has never been married and he has no children. In one of our more recent conversations we talked about our own dating experiences and those of our friends. What I concluded at the end of that conversation was this: no matter your age, dating can confound us all. Comparing my own experiences to his, though, I found that as a 27 year old, single female my outlook on dating and love seriously differed from his. Our conversation left me with a sense of curiosity about how dating differs across the generations. I then enlisted the help of single men and women from their 20s up to their 60s to provide feedback on what they loved about dating at their age, what they didn’t like, lessons learned, and dating advice they could offer others. What follows is a compilation of those responses.

Dating In Your 20s


Your social circle in your early 20s is pretty wide. You’re likely still in touch with high school friends plus all the new ones you’re meeting at college: classmates, members of your sorority or fraternity, recreation league members, party-goers. Really, there are endless opportunities to meet people because outside of your own social circle you’re introduced to a friend of a friend of a friend on a regular basis. Take your pick, there are a lot of fish in the sea.

This differs from your late 20s as people have started moving away, are in committed relationships, or are getting married and having kids. Hanging out with your friends becomes a less frequent activity and the idea of going out alone can be intimidating. You also find that once you start working full time, getting a solid 7-8 hours of sleep is far more appealing than partying mid-week until the wee hours of the morning. All of a sudden, the opportunities to meet new people become more scarce.

You also find that age difference isn’t as much of an issue in your late 20s. You probably even prefer someone older because of their maturity. And, especially if you’re a woman, you find that men in their 30s and 40s prefer to date someone in their late 20s, increasing your love prospects that much more.

The downside of your late 20s, though, is you start feeling the pressure of settling down and having kids. That ticking biological clock starts looming over your head as your family starts pestering you with comments like, “I was married with children at your age,” and “Your eggs are going to dry up.” The ticking biological clock hardly crosses your mind in your early 20s. It was a lot less stressful when dating was just about having fun, testing the waters, and gaining experience.

On the upside, you have a pretty firm handle on who you are as an individual whereas in your early 20s you’re still trying to figure that out. Your interests and what you want are constantly changing and with that comes some uncertainty. That uncertainty seems to subside more as you begin to understand what you expect out of a relationship and what you have to offer.


Without a doubt, it’s your uncanny optimism about love. For the most part, you aren’t tainted with cynicism like you are in your 30s and more so in your 40s and 50s, when cynicism towards dating is pretty apparent. Because your life and love experience pales in comparison to those who are older - those who may be tainted by the sting of divorce from someone they thought they’d spend forever with - you carry with you the blind faith that you’ll find ‘the one’. If a relationship doesn’t work out, you rebound fairly quickly and move on to the next person. In this regard, the rest of the dating world can learn a thing or two from you.


The pervasive hookup culture that characterizes your 20s makes it difficult to build emotional and intimate connections with another person. Moreover, it’s more common to just ‘hang out’ than to put in the actual effort of courting someone. You’re more focused on pretending like you don’t care and having the upper hand than you do about the relationship itself, which creates a sense of insecurity, lack of commitment, and immaturity. Putting a label on a relationship is so not your thing. Maybe that’s because of this whole ‘just hanging out’ mindset, which gives you the excuse to not form an attachment and to easily walk away. At this age, if you want a serious relationship you’ll likely be fighting this battle.

It’s no surprise there are definite financial constraints to dating in your 20s as well. There are a myriad of reasons for that - maybe you don’t have a job or you have an entry-level position that doesn’t pay all that much or your student loans eat up all the extra cash in your bank account. Whatever the reason, taking someone out for a nice dinner is all the more difficult. Even though financial constraints present challenges, the upside is that your dates can be more inventive and exciting than say a fancy dinner. With a limited budget, you get to know your city in a unique way either by going to free events or checking out state parks and historic attractions.


First things first: when you get older you realize that dating is more about companionship than it is about someone ‘completing’ you. You learn that you are an individual who has wants, needs, and interests outside of a relationship and that all of those things should be nurtured. When you’re younger, you equate relationships with giving yourself over to someone. If you want to be in a successful relationship, you have to change that sort of mindset. A relationship is a partnership. It is not about two people becoming one.

Second, as you get older, you find it’s not all that difficult to be yourself. There’s no need to fit a certain kind of mold. You’re comfortable with who you are. You aren’t that afraid of judgement. You have absolutely no tolerance for the creeps in the world. You are certainly more confident, which makes you more attractive. If anything, you should learn to embrace all of you now. Being yourself is easy.

Dating In Your 30s


The biggest difference between dating in your 20s and 30s is confidence. By now, you have a firm grasp on who you are, the qualities you are looking for in a potential mate, and the kind of life you want to live. You recognize the importance of your own happiness first so you spend your time pursuing individual interests and nurturing your career, friendships, and familial relationships. You know by now that ‘settling down’ doesn’t mean settling for the wrong sort of person.

That being said, you’re probably sizing up your date to determine if they have the potential to be your life-long partner. Could s/he really be the one? This is different from your 20s when you were mostly just concerned about having a fun time together. Now, you’re constantly looking for clues and evaluating their compatibility with you - do you share the same values, does s/he have their life together, does s/he have direction, is s/he aspiring to better themselves and achieve new goals? Sure, you still want to have fun with them but now you know that passion and similar interests will only get you so far.

Since you know what you want by the time you reach your 30s you have little patience for wasting your time on someone who ultimately doesn’t want the same things you do. You find that the deal breakers of your 20s vary significantly from the deal breakers of your 30s. Now, you’re less concerned with superficial things like physical appearance (although still a consideration) and more concerned with the bigger picture questions about marriage and children. Not only are the conversations heavier but they also come up a lot quicker than they do in your 20s. The rules and games you lived by in your 20s? You’ve thrown them out the window. Gasp. You’ve finally reached adulthood.

It’s also quite possible that all the heartbreak and failed relationships of your 20s have left a sour taste in your mouth. Maybe you don’t trust easily or you have a hard time opening up or you think that all women/men are awful. When you’ve felt that sort of pain, it can be difficult to get past those preconceived notions. While not completely gone, you do find that your optimism about finding love has dwindled.


The upside of all the heartbreak and failed relationships of your 20s, though, is that they taught you some valuable life lessons. You find it easier to articulate who you are, what you want, what you can offer, what your strengths and weaknesses are, and what may be a red flag. What that means is this: you no longer feel the need to hide or change yourself to match the other person. You are your own person and if someone doesn’t live up to your expectations you are going to walk away a lot sooner than you did in your 20s. The advantage? Less time wasted, of course!

And, let’s get right to it - you have better sex. You know what you want and you aren’t afraid to ask for it. You also know what you don’t want and you’re not afraid to say that either. All those insecurities you had about your body in your 20s (is my stomach flat, are my muscles big enough, should I shave or not shave ‘down there’) - eh, they’re less important now. Your main priority is simple: to enjoy it.


By the time you reach your 30s, it’s likely a majority of your friends are married, married with kids, or have kids. With a dwindling social circle, your busy schedule, and their busy schedule it becomes harder to meet people. That makes dating in your 30s trickier than it was in your 20s. It may have been hard to meet people in your late 20s but it’s certainly more difficult now.

So then maybe you give online dating a shot. You might be new to the online dating scene or perhaps you gave it a go in previous years but now, with fewer opportunities to meet people, you’re taking it more seriously. What is challenging about online dating is managing your expectations. With match-based sites often comes disappointment because many of the people you’re matched with may not be exactly what you expected. You love to travel, they don’t. You’re an active person, they prefer sitting on the couch watching movies. You like sports and tailgating, they aren’t remotely interested. They have a slight gap in their front teeth, you have perfectly straight, pearly whites. Being matched with someone who doesn’t match up to a version of you can certainly be frustrating and it may even encourage you to write online dating off completely.

Dating in your 30s can also be more complicated, particularly when it comes to having children. Maybe you or your date already have kids. Maybe you don’t want kids or can’t have them. Regardless, the topic of having children comes up fairly early and can be a deal breaker in moving forward with a relationship. Being honest about your views on having children can be awkward and sometimes, depending on your stance, it can shrink the dating pool even further. Moreover, when it comes to dating someone with children, there are going to be competing attachments as you’re both vying for the other’s attention. Not to mention differences in priorities. Their child comes first. Your relationship comes first. Without a doubt, this can make you two butt heads every now and then.


Speaking of kids, the greatest pressure of dating in your 30s is the ever elusive ticking clock. By the time a woman reaches their mid-30s her fertility greatly declines, thus the desire to have children (if you want them) can cause some unnecessary desperation early on in a relationship. This holds true for both men and women. If you carry that desperation with you there’s a good chance you may scare someone away before they even have the chance of getting to know you - or vice versa.


Be intentional in your pursuit of love. If you find it difficult to meet new people then expand your current social circle. Join a recreation league. Give online dating a shot. Try that yoga class. Volunteer for a cause you are passionate about. You’ll never meet someone by sitting on your couch at home alone.

Don’t compete with your friends to catch up where they are in terms of marriage and children. It’s more important to have all that with the right person, so don’t let your desperation for raising a family get in the way of that.

Consider your children if you have them; their needs are important too. You don’t want to get so wrapped up in finding a suitable step-mom/dad that you end up making them feel like they’re being replaced. Also, if you don’t have children, decide if you are willing to date someone with a child or if you even want them. The topic of children can be a deal breaker but being honest about where you stand on the subject is the right thing to do for the both of you. Don’t bring it up on the first date, but address the topic early on.

When it comes to online dating, keep in mind that the purpose of this whole process is to move beyond immediate physical attraction and mutual interests. The whole idea is to break free of your perfect match and be open to meeting all different kinds of people. Remember, you are both individuals outside of the relationship. There will be commonalities, but there will also be differences. Be okay with that.

Dating In Your 40s


The biggest advantage people have dating in their 40s over younger generations is that you are more sure of yourself and your life values . You aren’t willing to compromise on the things that are most important to you. You know your priorities. You can spot a bullshitter a mile away. You know all the red flags and have no qualms walking away as soon as you see them. It’s a super power, really. Own it!

There are other advantages as well. Like that checklist you carried with you in your younger years - the one that detailed all the characteristics of your ideal mate - well, you’ve thrown it to the wayside. Compatibility and personal characteristics take precedence over the superficial ones, like physical appearance. While a healthy relationship with sex and your significant other plays an important role in being satisfied in a relationship, you know that it won’t be what keeps the relationship going. What does is true emotional intimacy - the ability to communicate and have thoughtful conversations with one another.

That being said, at this stage you really aren’t feeling the pressure of the ticking biological clock so there isn’t an unspoken expectation to get married and have kids. Without that big elephant in the room, you can focus more on enjoying each other’s companionship and making sure you two are ‘right’ for each other.

Compared to your younger counterparts, you’re more cognizant of your mortality and that life is too precious and short to spend your time worrying about the small stuff. If life experience has taught you anything, you know the importance of living in the present moment and letting trivial issues roll off your back.


In all likelihood if you’re dating in your 40s it’s because you’ve gone through a divorce or have ended a long-term relationship. You’ve probably been married awhile so when you find yourself back in the dating scene you forget how it happens or what to do or say. Your self-confidence may be bruised from the divorce or you might be suspicious and question every little thing about someone you meet or maybe you even question your own judgement. Regardless, it leaves you with a sense of uncertainty and getting over all that proves to be quite difficult.

Many 40-somethings also note that while there may be plenty of potential matches out there it’s difficult to find a quality date. Couple that with the profound hurt and pain that comes from divorce or the ending of a long-term relationship, it’s no wonder you may hold a bit (or a lot) of cynicism on the subject of love. Cynicism is a far easier emotion than optimism but the only thing it does is give you the permission you need to stay single.


In your 30s, there’s a 50/50 chance that children will factor into your relationship. In your 40s, though, children will undoubtedly be a consideration with almost anyone you date. Whether you both have children or only one of you does, there’s always going to be competing attachments. Nurturing both relationships is equally important and you have to consistently assess the potential of both of your lives merging. Are you prepared to go from single mom/dad to a stepfamily? How are your kids (or his/her kids) coping? When children are involved, there is a lot more to consider and your relationship will (or at least should) move more slowly.


If you want a quality date make sure you’re a good picker. Be honest about what you’re looking for and don’t jump into the dating pool trying on different people to see how they make you feel. By now, you know what you want. You know who you are. You know your life values. If you have an online dating profile or you have a professional matchmaker or you just meet someone at the hot dog stand, make sure the person you portray is a true reflection of those characteristics and not the person you think will garner the most interest.

Accept that there’s going to be baggage but more importantly realize that baggage doesn’t have to make your dating experience a doom and gloom show. If the person you are dating has views different from your own, make an effort to understand why. You have your deal breakers and red flags and you should most definitely stick to them. But if their differing views are not deal breakers give them a chance. Just like you, they may be cautious or guarded because they’ve been hurt.

If you’re wary of online dating or you just haven’t had much success, enlist the help of your friends. Welcome blind dates set up by your friends. They know you. They know the other person. There is a reason they think you might be a good match. If your friends know you’re looking for love they’ll be there to support you in that journey. If you ask for their help, they’ll be more than happy to play a role in helping you find that spark with the next person.


You may be annoyed with the younger generation but there is something to be learned from them: that uncanny optimism for finding love. They are fearless in taking risks and they are open-minded and they know that despite their failed relationships they will find someone who makes their lives infinitely better. Let go of the myth that there are no good single men or women out there. There are. If you shift your perspective and let go of that cynicism you will undoubtedly see them in flocks.

Dating In Your 50s And 60s


At this age, it seems like everything has changed but in many ways nothing has changed. No matter how old you are, dating can seem scary but at the end of the day it’s still about getting to know someone, forming and nurturing your connection to one another, communication, and knowing what you’re looking for. That age old advice you give to your children as they embark on their own dating experience remains true for you too: keep an open mind, have fun, and always be honest.


It’s true though that a lot has changed. The biggest difference between dating in your 20s and dating in your 50s and 60s is easily the way you think about your future. In your 20s, the future seems far and distant. In your 50s and 60s, everything you imagined has become your reality. Your age is showing. You’re more conscious of your health. You fear death in a way you didn’t used to. You’re nearing retirement or are retired. You hardly thought about any of that when you were younger. Your life changes in many ways, such as your looks, activity level, and financial situation. Essentially, the things you worried about when you were younger seem trivial compared to what you worry about now.

The reason why you’re single is also profoundly different. Most likely you’ve gone through a divorce or are a widow. The sense of loss both of those experiences bring can impact your dating life in many ways. If you’ve been burned by divorce once (or two or three times), you may not be eager to try it again. If you lost your partner because of death, you couldn’t possibly imagine anyone replacing them (they can’t, by the way). For these reasons, you’re probably not looking to get married again. You just want companionship - good conversation and laughs - which means there’s a lot less pressure to settle down.

Time has an effect on your body and physical appearance as well, which can impact your self-confidence and provoke some fear about the ‘big reveal’. Unlike the younger version of you, though, you have a lot more experience in the bedroom. Fewer questions and less fumbling around means you can revel in the romanticism. Own your sexpertise!

Keep in mind, though, that you’re equally at risk of getting a sexually transmitted disease as you were in any other decade. In the survey, many people in this age bracket noted that a benefit of dating at this age is you’re either infertile or you’ve had a vasectomy so using condoms seems unnecessary. There isn’t a threat of accidental pregnancy. But this is far from the truth. Sex is primal at any age. Taking care of your health is important. Just wear them.


Take it seriously! Whether it’s joining the online dating world or getting help from friends and family you have to be intentional in your pursuit. You have to be honest about your values, what you want, and what your expectations are. At this age, you’re pretty set in your ways so making sure you have common values is key.

When you find yourself dating again after the death of your husband or wife, you can’t fathom ever loving someone else as deeply. They could never be replaced. You’re right in one regard - no one can take the place that person occupies in your heart - but you can find love with someone else. Fairy tales and fantasy teach us from a young age there is only one soulmate for us. But is it so impossible to believe you are compatible with more than one person in this world? No one will ever occupy the space your husband or wife did, but our hearts are big. There are many soul mates out there for you and they come in many forms. Don’t equate finding that compatibility with someone new with replacing the one you chose to spend forever with.

Don’t be afraid to involve your friends and family in your new dating adventures. Tell them you’re ready to meet someone new and be willing and open to them setting you up on blind dates. Interestingly enough, you’ll also find that your adult children are giving you dating advice which seems unnatural and weird. Accept their advice with a gracious heart.

At the same time, be aware that even though your children are grown they may still feel uneasy about you dating again after the death of their mother/father or your divorce. Of course, that shouldn’t prevent you from dating again. Eventually they will come around but know that you dating again can make them feel uncomfortable, which is perfectly natural.

Love is exciting and meaningful at any age. At the end of the day embrace life, enjoy the journey, and be true to yourself.

Lindsay Wallace

Lindsay Wallace is a blogger and contributing writer to Taylor Magazine, Elite Daily and Ambiance Matchmaking. A travel and outdoors enthusiast as well as a mental health advocate, her inspiration for writing comes from emotion and the desire to share her experiences in hope it may help others. Lindsay currently lives in Madison, WI with her dog, Miley.

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