Dating in your 30s as a man is common in today’s society; divorce rates are higher than they were in the past and many women are encouraged by bad relationship advice blogs to be hypergamous, branch swinging from one relationship to another instead of building one committed relationship. Many men also find that during their 20s they haven’t had the time to build up wealth and without resources such as a home to provide so they find it difficult to attract a woman who wishes to settle down and marry. So if you are looking for advice on dating in your 30s as a man you are not alone, and you’ve also come to the right place to get some advice on how to date better during your 30s.

Have You Been Experiencing the Vicious Cycle of Dating?

Have you been dating around with no luck in finding a match to settle down with? Are you unhappy being a man who is still single in his 30s? Have you invested your time in the typical dinner and drinks routine, and still haven’t found a romantic connection?

One of the main reasons men find themselves single well into their 30’s is because they got distracted with their careers. Although having a strong foundation for a career is a wonderful blessing, that same career can cause many strains within your personal life. The initial time investment a new profession requires could leave you lacking experience in the dating world. Luckily for you it is becoming more common for a man to find romantic connections later in life, even well into his 30’s.

You are never too old to begin exploring new relationships and to find the perfect person that will complete your life. Again, a stable career is a great blessing, but at what cost to your personal life? Are you willing to continue to give up any idea of a romantic life to keep your career, or are there ways you could compromise? 

It can be extremely confusing and challenging to sort your emotions when you are older and single. You may be looking around to discover that all of your friends have been starting families and moving into different stages of life, all while you remain single. It can also be emotionally difficult not having a stable intimate emotional relationship throughout your everyday life, as having a mate is instinctual to all humans.

You are still more than capable of finding quality women to date. Whether you are single due to a bad break up, a divorce or have just been too busy to date seriously, you can still experience dating and all of the fun it has to offer as a single man in your 30s.

Dating as a Single Man in Your Thirties Can Actually Be Great

The great news is that if you are single the game is not over! Many people may lead you to believe that it is too late in life for you to begin new relationships but the truth is that many men don’t really acquire the qualities that marriage minded women are looking for until they are in their thirties . So if you find yourself asking if it is too late in life to start new relationships, the answer is ‘No’. This could actually be the best time for you to start dating.

Barney Stinson from How I Met Your Mother is an example of why your 30s are the best time for men to date.
Barney Stinson from How I Met Your Mother is an example of why your 30s are the best time for men to date.

People who say that your 30s is too late in life to begin new relationships could not be more mistaken. While yes, dating can be quite challenging and dating in your 30s as a man can be even trickier, you should now at a time in your life when as a man you have the most options in the dating pool. You can date younger women and you can date older women. During his 20s, unless a man is a prime physical specimen he will struggle to get older women interested in him as he typically lacks the financial means by which to take the woman on dates to fine establishments, theatre plays, amusement parks and other sites that make the best date environments. While popular media encourages men to take women to the movies as a date, this really isn’t the best environment because watching a movie together does not give you much opportunity to talk with the girl and can be awkward for you both to sit and watch a film with basically a stranger. Yet taking a girl to the movies is about what most men in their twenties can afford to do, as most men are working hard at college and unable to afford much in the way of romantic dates. This also means most of the women a man in his 20s encounters are other girls attending the same college, and dating apps do not necessarily help you find other women as most women on dating apps are in their thirties — and who are generally uninterested in younger men due to social pressures, as well as the young man simply not having the financial means to be a provider. The vast majority of women on these dating apps are also not childless; overwhelmingly they are single mothers, who may even have multiple children. So the idea of them dating a man who doesn’t have a home, a car and the financial means to provide for her kids will usually turn her off.

Sadly this is the reality of dating today. Far too many women are having children with men they are not married to, and who only realize late in life they should have first figured out what qualities make a good man before having children with the first guy they have sex with. This is not to say that you should completely avoid dating single mothers, as it is pretty much impossible to avoid them in the dating pool as they now make up the majority of women on dating apps. Rather what I am encouraging you to do is try to find the best women you can to date during your thirties and to settle down with, childless or otherwise. It is possible a single mother has learned the errors of her ways and is now trying to be a Cinderella instead of a Tinderella. Dating a single mother comes with it baggage; a host of responsibilities and obstacles that you will not otherwise have to deal with. So whether you want to date single mothers or not is a choice you will have to make on a case by case basis as you experience dating as a single man in your 30s.

Having said this, let’s focus on the positive; your thirties should be viewed as a very exciting season in your life. Be optimistic through this phase because you have a whole world of new experiences waiting for you around every corner and dating is just one of them. Every date you go on can be different and every girl you meet will be different. It is up to you to discover which girl will match your lifestyle and goals in life.

The Traditional Way of Dating Is Dead

Let’s face it, the traditional way of dating that everyone has been taught just doesn’t exist for most men anymore. We are told that we will date during our teens and 20s, get married before 30s, have children, raise those children with our wives and then grow old together; that is how it is all supposed to work, right? This is the traditional picture that people always talk about for how life is supposed to go and it is referenced in many movies, novels and other media. Yet that ‘traditional’ path is closed to most men today.

Society is ever-changing, and unfortunately not always in the best ways. Concerted efforts by popular media to promote alternative lifestyles has resulted in many women desiring to be hypergamous; to date around with as many partners as they can in search of ‘the one’, some mythical soul mate person who doesn’t actually exist, as we talk about in our article on the subject. Women are often encouraged by bad relationship advice blogs written by other miserable women to be what we here call the Tinderella; a woman who does not believe that men deserve her loyalty and is primarily fixated on having relationships to satisfy her fragile ego rather than going to counseling to deal with her psychological issues. This has resulted in many women in their 20s making very poor choices in their relationships, such as having children with loser men in their 20s who don’t have careers or ambitions, and who sleep around with other women while the girl is sleeping around with other men trying to find someone ‘better’. Both end up cheating on each other, and often the girl ends up having children by one or more men who won’t be good fathers before she turns 30. Some of these women have an epiphany in their 30s and realize the traditional path would have worked much better, and now try to find a ‘good man’ to take care of her children she had with loser men; the effort usually does not work out unless she marries a man who already has children from another marriage and is in a similar situation; unable to find a childless woman to date him.

The narrative many of these desperate women have created now is that men should be simps to her, showering her with gifts and money simply for being pretty in exchange for her time and sometimes even sex. Ironically many of the men who become these simps are men who were the same losers in their 20s who lacked ambition and fathered children outside of marriage. They end up becoming simps because their only market value — their looks — has already faded after spending their twenties drinking and smoking heavily, and other hard ways of living. And because they are now in their 30s and have dropped from a 10 or 9, now down to a 6 or lower they find it difficult to date beautiful women anymore. Lastly these men usually have very little wealth because they never put in the effort during their 20s to have a career so they are now worse than they were in their 20s. So these men may become a simp in order to spend what little money they have getting small amounts of attention from a woman.

(You should know that if what I wrote applies to you and you are reading this article, welcome because by reading The Millennial Gentleman you will figure out how to get clean up your act and your life back on track).

However if you spent your 20s making an effort to follow that traditional life path then you should have completed education or some other course that taught you valuable skills that help you generate wealth. You should have a car and some place consistent to live, whether it is an apartment, house condo or in my case, a luxury Airstream travel trailer that I live in as a digital nomad vagabond. You have disposable income that can be spent on dressing and grooming well, and able to afford to go to nice restaurants, amusement parks, theatre plays and other good dating venues that create opportunities for intimacy with women. This means that you will usually find it easier to get dates in your 30s than you did in your 20s because you have more to offer a woman who spends time with you.

Dating in Your 30s as a Man is Not Always Fun

This is not to suggest that dating as a single man in your 30s is always fun. Indeed, dating will not always be as enjoyable as you might want it to be! As mentioned before, bad relationship advice blogs written by unhappy women encourage many women to be Tinderellas, and they will make you miserable if you permit them to do so. It has become cliché to meet a woman for lunch only to have her spend the entire date ranting about politics with a religious fervor, and for that to be the only subject she is interested in discussing with any attempts to shift the conversation to topics that actually matter in a relationship, such as future goals, lifestyle quirks and anything else people figure out about the other while making small talk on a date.

There is now a very large amount of women who, instead of having a personality have an ‘identity’ that comes with a pre-fixed label, and they work hard roleplaying to conform to the stereotypical ideas about these labels so they can be trendy. While being a gentleman might be considered a label too, it actually is not one intended to guide all of your decision making; The Millennial Gentleman doesn’t tell you what your politics should be. We simply tell you how to behave as a man in order to attract a high quality woman and what steps you should take to present yourself to others in order to obtain the most success from your interactions with others. We actually suggest you don’t talk about politics on a first date; there are reasons why our grandparents knew politics was a subject that shouldn’t be discussed over dinner.

So, should you find yourself on a date with a woman who is more interested in ranting to you about political events she is infuriated by rather than about trying to convince you that she is the kind of woman that will make a good wife and mother, then the best thing to do is to respectfully end the date; say you just do not see this as working out. Pay the tab for the date and leave. My opinion is that women who give bad first date impressions are not showing you even a fraction of the iceberg of crazy that they are still hiding, so if you see erratic behavior on the first date you should expect a great deal of future drama if you choose to keep being involved with her. These women need a therapist, not a boyfriend.

How to Stay Motivated While Dating in Your 30s as a Man

Over time dating around is sure to wear on you financially and even emotionally. The art of dating is not as simple as it may appear. There is much more behind dating and how to make it successful for the long haul. And if you are going on a lot of dates then you are sure to have some memorable stories that you will be able to share for a lifetime. That being said, being a single man in your 30s should not be viewed as a negative, but instead viewed as an opportunity.

As a single man dating in your 30s you get to explore many different kinds of options in the dating world and you get to play the field until you find your Cinderella. You have the chance to experience countless new adventures in the realm of dating, trying all kids of trendy date ideas like escape rooms, 3D VR arenas, amusement parks and so on. You also no longer need to simply meet for dinner or drinks and then end the evening; the night can continue because you can hit up wine bars, or if the night is going especially well even invite the woman back to your well decorated bachelor pad.

There are so many different types of dates that can be very fun and unique you can do during your 30s that you couldn’t have afforded during your 20s.

Finding Potential Dates In Unique Places

Ignore what the naysayers in the mass media say; women still appreciate men approaching them in the real world and asking them on dates. There are no rules out there that say you must find romantic connections by using online dating apps only.

Many men have been so focused on using dating apps that they forget the traditional way to date is used by asking out women you already know, a friend of a friend, picking up a girl at a bar, or simply hitting on a girl you meet in passing. When you consider those options still exist and the opportunities to meet woman are endless but they do take more effort than swiping right on a phone screen.

If picking up a girl at a bar does not comes naturally to you, there is no shame in that as unfortunately many men were not taught by their fathers how to do so. For some advice on how to attract a woman and approach her at a bar, please read our article on the subject, How to Become More Attractive to Women.

Bars are ideal locations to pick up women, as the atmosphere of a bar tends to create a setting for people to loosen up. Many women go to bars specifically because they want to be approached by men and hit on. So these are a great environments for you and others to relax and get very comfortable in while still in a public setting. Additionally if you are not feeling a connection, bars also offer an easy escape route to make a clear, easy exit by simply getting the check and saying goodbye.

There are also excellent local spots to meet people in every city, which are specific to your city. All you need to do is conduct a little research to find out where single people tend to gather in your city. There are also speed-dating events that occur to help you meet several potential partners in a short amount of time. There are no limits or constraints on where you can find a romantic connection in today’s society. Everyone is connected at all times, and the opportunities to date are truly endless. 

Online Dating Opens Countless Doors 

With today’s technology it is easier than ever before to find romantic connections anywhere and anytime. Back in the day I first started using the internet, meeting people online used to be scary and not as popular of an activity. However, over the years it has become much safer and widely popular among single men and women. With so many dating services available online it is so simple and easy to meet new people with just a few clicks. If you have a good looking photo of yourself to add to your profile and are able to describe yourself well, you could find yourself out on multiple dates in little to no time. Therefore, the online dating apps can be an excellent starting point.

There are countless dating sites available, allowing people to have a huge pool to select partners. A few of the top most popular dating sites that people have used in order to get more experience within the dating world would be; Tinder, Eharmony, and Match. One of the biggest draws to these online dating sites is that most of them can cater to their users’ particular interests. For example, there are dating sites that gear towards individuals seeking farmers, religious people, or even a specific age range. Whatever your personal requirements or desires may be; online dating has numerous options for your dating lifestyle. 

Push the Boundaries of What a Traditional Date Is 

Opting for a more fun and unique date idea allows the two of you to open up and experience different sides of one another. When you are a single man in your 30s you are most likely looking for a more serious and deep connection. You are trying to date around to find a partner you can envision yourself with for the rest of your life. Therefore, you should try and experience various activities to understand best how each of you will react in different situations. This is also a great way to find someone to do something with you that you always wanted to do but can only be truly enjoyed with another person.

Several unique date ideas are included below. These ideas will inspire you and your partner to hopefully experience some great quality time together in order to grow more intimate. 

Fun and Unique Date Ideas 

  • Swap a dinner date for a breakfast date 
  • Go for dessert instead of drinks
  • Outdoor Activities, such as hiking or skiing.
  • Invite a woman on a camping trip 
  • Act like kids and go to an amusement park
  • Minatare golf
  • Sports outing, such as a baseball, basketball or hockey game
  • Play board games at a trendy gaming themed bar
  • Have an extended weekend vacation at a breakfast and bed
  • Visit a winery
  • Take a cooking class 

Whether you are looking to merely pick up a girl at a bar or settle down for the long haul dating in your 30s as a man should be nothing short of an adventure. Be prepared to step out of your comfort zone and try a novel date idea. Sometimes what two people need is an exciting adventure to see the best in one another.

Dating for Fun

The best aspect of dating is that your 30s is that you have enough accumulated experience built up in your life that you can have good conversations with women. This is the time in your life when you can best have long intimate conversations about your dreams, aspirations, and end goals with a woman and she is most likely to take you seriously about them. These special dates are when you will have intimate moments where the two of you will discuss what future you may or may not want to have with one another. Many people desire marriage and are constantly on the lookout for their perfect match when they are dating around. However, marriage may not be the right path for everyone. If you have no interest in settling down permanently, that may be acceptable with your partner if you are open and honest from the beginning. The best part about dating is that you can make your intentions known from day one not to deceive anyone.

Dating In Hopes of Finding Commitment 

Again, there is absolutely nothing wrong with dating to have a good time, become more adventurous or to get yourself out of your comfort zone. However, if you are not simply looking for casual dating and hookups but instead are looking to make a commitment, then dating around in your 30’s as a man may take more time in order to find your soul mate. It is not to say you cannot find a good partner; however, it may just take a little more time as it is getting harder and harder to find quality women who want to get married. In general, once you reach your 30’s people are typically more curious about slowing down the dating process and trying to invest in their relationships, and this applies to women, too. Women in their 30s are more likely to be trying to find a long term life partner and are over their party days. You should try to find a woman who has already done the casual dating stuff, and is now more dedicated to getting married.

The easiest way to not waste time is to be forward about settling down as your goal; women who find this “creepy” were not truly interested in getting married anyway and you will waste a lot of time and money dating them. Be forward and say you are dating because you want to get married and settle down. Any woman who wants to be more casual has no interest in doing so; even if she does have an interest in you it will only be a short term one until she moves on to the next guy.

Enjoy Dating in Your 30s as a Single Man

As mentioned at the start of this article, dating in your 30’s as a single man may initially seem to be challenging and difficult. However this is a time that should be embraced. You have had years to grown as an individual and know exactly what type of person you are looking to spend the rest of your life with as a partner. You know your pet peeves, and you know your deepest desires. You should have also acquired some wealth now, and have disposable income to enjoy the night life. Having more financial freedom later in life allows for better date experiences.

This is an incredible time in your life. Yes, it can also be a frustrating time with the current pool of women in society, and it is acceptable to feel underwhelmed by the women you meet. However you should try to use these dates as an opportunity to discover a new side to yourself through dating. Uncover what you like and what you are looking for in your partner and do not settle for anything less than what you deserve; which is only the best.


Carey Martell is Editor in Chief for The Millennial Gentleman. A thirty something modern man who is politically independent, non-religious but a firm believer in ideals of chivalry and traditional family values. Carey lives his life as a vagabond digital nomad traveling and living life to the fullest while managing his businesses remotely with a laptop and internet hotspot connection.