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Online Dating Tips for Men Over 50

I'm a boomer and I've used online dating sites and would like to help others navigate it to find what they want.

I am a woman who has used online dating when it first evolved and I was a younger person. Later, when my marriage ended and I was over 50, I used it again. For me, it was an easier way of meeting more people than I could have out in the real world. My experience taught me quite a lot.

I have noticed some common mistakes in online dating efforts so I decided to offer online dating tips for men over 50 given from a woman's perspective. Now obviously, not every woman is the same but the advice I have here would probably be useful in trying to meet the majority of women online.

#1 Define What You Want

Just as with any new project it's good to sit down and imagine exactly what result you want. Think about what you must have, what you would like to have, and what you can't accept. This may include considering things such as:

  • What type of relationship you're seeking. For instance:
    -- casual dating
    -- FWB/nothing serious
    -- marriage
    -- long-term monogamy, etc.
  • The type of person you would like to meet. For example,
    -- a working professional
    -- someone who is retired
    -- someone dedicated to a healthy lifestyle and fitness
    -- someone outgoing and highly social
    -- someone less outgoing and more focused on family, home, etc.
    -- someone who is worldly and well-traveled
    -- someone who dresses well and maintains a nice appearance
    -- someone more down to earth and casual
    -- someone with no children, adult children only, or no children nearby
    -- someone who shares your religious (or perhaps political) beliefs
  • The types of things you want to be sure you can share, such as
    -- spectator sports
    -- outdoor adventures or active involvement in sports
    -- social activities
    -- travel
    -- hobbies
    -- involvement in a religious organization
    -- cultural events
    -- volunteerism
    -- stimulating conversation
    -- retirement goals, possible relocation
  • Distance
    Be realistic. Certainly, some individuals have established and maintained relationships from hundreds of miles away. But you know yourself, will you have the energy, commitment, and time to do that?

    On the other hand, if you will only date people within 20 minutes of you, why haven't you already found them? They apparently live in your neighborhood. So think through the distance you are willing to accept.
  • What are your deal breakers? Some examples might include:
    -- smoking
    -- minor children at home
    -- unemployed or obvious financial instability
    -- multiple divorces

#2 Approach This Project Realistically

There are a few things to think about as you make your list of wants, must-haves, and deal breakers if you want the best chance of success. Keep in mind:

  • Sure, the more specific your match criteria, the more targeted your responses and fewer time-consuming contacts that aren't right for you. But, the more specific you are, the more likely you might miss out on someone who surprises you. (sometimes we want things we didn't even know we wanted) For this reason, it's best not to make a laundry list. Women are real people, just like men. You shouldn't be looking for perfection or some Hollywood version of an ideal woman. Stick to your deal breakers and deal makers.

    You might not want to presume you know what a person will be like based on their education or their age. You don't want to miss a gem. There are some women over 55 who are more fit than many women in their 30's. There are some women in their 30's who are more emotionally mature than some women in their 60's. A woman with a high school education but a curious and active mind may be an enthusiastic lifelong learner who is more stimulating than the attorney who can discuss only her work.
  • You may need to stop and realize what suits you now, may not be what suited you when you last dated before you were married. If it has been 15, 20, or more years, your needs, desires etc. may be different. You may consciously need to think about it.

    First the obvious. Young women will still be attractive to you and sometimes they will make a great partner. But for the average guy, restricting your eligible matches to women 10-15 years younger will only result in frustration. You will be limiting the number of women who are interested in you, an older man.

    Other traits that are desirable should also be assessed to be sure they are still what you need. Is it still important that your potential partner enjoy dance clubs? That they are career focused or driven to succeed? That they have a wide social circle or can accompany you on your marathon runs? In some instances, your needs may have changed as you've learned more about how partnerships work or how your life has evolved.
  • Assess whether or not you have the time for this project. Coming into a relationship as a whole person with a full life is good. However, establishing a relationship requires some consistent contact. If you have a full-time job, your own business on the side, kids you still see every weekend or two, and buddies to spend time with on a regular basis, you will find in many cases the women won't stick around waiting for you to make time for them every third Thursday. If you're honest, you probably wouldn't for them either. For a good relationship to grow, it needs to be a fairly high priority.
  • Assess your level of flexibility. When we are young, the focus is on building lives together. When older, you've already defined what your life is about, what you like, what your major goals are, and so forth. Are you able to leave space for the influence of another person? Or, will you give your potential partner a narrow slot to fit into where, in order to be with you, they have no part in building your joint life? If that slot is too narrow, no one will fit into it. For instance, if you want to live life on the road in your RV, spending every winter with your kids in Louisiana, and allowing your old army buddy to bunk up in your place each summer then the number of potential partners will be drastically cut down as your plans are likely to conflict.

#3 Show Your Best Side

Once you know what you do and don't want and feel you are ready to get started, you need to choose your online dating site and develop a profile. Your photo on your online profile is important. Men are more visual than women, but that doesn't mean that women don't care what you look like.

  • Your main photo should be of your face. You should not have on sunglasses in this photo. Ideally, no hat. It should also be close enough, that those who come across your profile can see your features. Don't even think about using photo editing.
  • Smile. If we gaze at your face we want it to be welcoming, happy, approachable, and to make us feel that you are smiling at us.
  • Include a full body photo.
  • Your photos should be recent. Ideally within the last year, but certainly no more than 3 years old.
  • Even if all you can manage is a selfie, make it a good one. Focused, well lit, and from straight on more or less. No looking down into the camera, no flash glare from a mirror, and no blocking your face with the phone/camera.
  • Dress nicely. No, you don't have to put on a suit, although that's fine. It's best to have on a collared shirt with sleeves, even a golf shirt will do. Athletic wear is acceptable, but in general, most women don't prefer to view you sweating it out at the gym or showing off your physique without a shirt on.
  • Photos of you doing what you love are useful too. Pictures with a pet are ok also, but photos of a kill made on a recent hunting trip will turn away more women than it will attract. If your photo shows you sleeping on the sofa or lying in bed, then viewers will assume that is one of your favorite things to do.

#4 Avoid Writing a Profile That Will Repel Most Women

There are a couple of basic things that can help you avoid writing a profile that will repel women.

  • Avoid negativity. Complaints about your ex, certain types of women, and too much information about what you DON'T want will send many women clicking away from your profile. It doesn't matter if the negative comments are about someone else, they still make you appear to be harsh and critical.

    Focus on the positive. You generally don't have to mention "no cheaters", "no liars", etc. Say you want "an honest woman who is also searching for a monogamous relationship" if that is what you want.

    Another problem can be the statement "no drama". Well, who likes drama? Drama queens are real and no one wants to deal with them. But, when someone says "no drama", half of the women will hear, "If you bring up an issue, I don't want to deal with it. As soon as there is a problem, I'll be gone."
  • Leave your baggage in the trunk. Don't use your profile to complain about your ex. Additionally, under no circumstances use name calling. Use of the term "crazy" is an example of name-calling that doesn't make you come off as a gentleman or as someone who can look at past relationships objectively and learn.

    Remember, you are involved with online dating so that you can move on, not so that you can air any old grievances. Focus on the future, not your past.

#5 Write a Profile That Will Attract the Right Woman

Writing a profile can be painful. Not everyone likes to talk about themselves and not everyone has terrific writing skills. After reading a few dozen profiles you will find most of them say the same thing, so you give up and just say "I am a good man, looking for a loving woman". This is not useful.

Take some time and tell people what matters to you, who you are, and what you want. We all want to be loved for who we are, so be who you are. A couple of examples:

  • "I'm a great father who has raised three successful kids. I go to work every day trying to help 30 kids learn how to solve algebraic equations and become good human beings. I love to grill in the summer, coach basketball, and plan weekend getaways with someone special because I love finding new places to explore. In my off time, I like completing home projects, going to the gym, fishing, and enjoying foreign films. I'm hoping to find a partner for life but I'm fine letting things progress slowly. I'm not perfect, but I'm a good listener, I know how to be grateful for the people who love me, and I want to map out my retirement with someone who can help plan our future adventures together. A woman who has an interest in travel, prefers an ice tea or lemonade over a Margarita, and could embrace more grandchildren would be my dream."
  • "I'm a busy executive who is an empty nester, works out 5x/week, and travels across the country routinely. Who am I? Well, I prefer tropical beaches vs mountain cabins, a round of golf vs. hunting or fishing, theater vs. movies, art galleries vs. festivals, and sarcasm vs. slapstick. I'm looking for a long-term partner who is comfortable mixing and mingling with people from a variety of cultures. She should be independent, health conscious, know how to dress well, conversant on a range of topics, and able to keep up with me. We will enjoy time together at the end of a busy week, out on the town, or alone together at home."

How much you write is up to you, but make your words count and let them help you find the type of person you want. A good profile is a sales piece and tells the reader what makes you a good man and sets you apart from all of the other profiles that say very little.

#6 Communication Tips

Most online dating sites offer the ability to chat or at least email each other before talking on the phone or meeting in person. Here are a few tips regarding that communication:

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  • If you wouldn't say it in person or in real life, don't say it online. For example, it's perfectly normal to want to see what someone looks like before attempting to establish meaningful communication. Therefore, if someone doesn't have a photo it's fine to say something like, "hey you sound really interesting and I would like to learn more about you, could you share a photo of yourself?"

    On the other hand, if someone has a picture or two posted, it would be inappropriate to say, "I want to see more of you, can you post more photos?" In real life, if you met a woman behind the counter at a bank and you could see her but not entirely, you would probably initiate a conversation but you would not say "hey, could you stand up and walk over here so that I could check you out front and back?"
  • If you are going to chat, chat. It's not impressive to ask someone to chat and then to respond only every 5 or 10 minutes or to give only one-word responses. It's kind of like having dinner with someone who is completely absorbed in their phone rather than you. Not a good first impression, so avoid multitasking.
  • If you are emailing back and forth, let the other person know if you are going to be MIA for a day or more. Adults have busy schedules and that is perfectly fine, just let the person know you will be out of communication as a courtesy.
  • Show interest, ask questions. Talking about yourself can show openness, which is great and shows you aren't just a passive participant. But you also want to learn about the other person and demonstrate a reasonable level of communication skills. Asking questions is the best way to do this. Take notes if necessary to help you in future conversations.
  • Once you've been talking for a while and know the basics, dig deeper. You know this new person is a nurse, what drew her to it, has she ever wanted to do something else? You know she loves to travel, where is the one place she would most like to go and why, what has been her favorite trip thus far?

Listening and being able to ask questions that allow you to really get to know someone is what good communication skills are about at this point.

#7 Don't Send the Wrong Message

Online dating poses some unique risks, for women and men. Here is another word of caution regarding communication related to these unique risks:

Don't immediately ask a woman for her phone number, address, email address or give her yours and ask her to contact you off of the site. Phishers and scammers do this. Use the safety of the site for your initial contacts.

#8 How to Communicate Rejection

You will be contacted by women you are not interested in getting to know. In my experience, the best practice is to let them know immediately that you don't wish to communicate. Short, definitive, but polite or kind. You can construct and reuse a simple message that suits the purpose, for instance, something with a polite acknowledgment of their contact, your dismissal, and a polite close:

  • Polite openings:
    -- Thank you for reading my profile.
    -- Thank you for your message.
    -- Hi, thanks for contacting me.
  • Dismissal
    -- However, I am focusing my search on local women.
    -- However, I am focusing my time on getting to know someone I met earlier
    and am not trying to meet anyone new.
    -- I've read your profile and just don't feel we would make a good match.
  • Polite Close
    -- I wish you the best in your search.
    -- Wishing you the best in your search on (Name of Website)

If you have been in communication with someone for a while and have decided you don't wish to meet or pursue anything further, a message with something a bit more personal is preferable.

Many online dating sites allow you to like, send a wink, a smile, or something similar to indicate interest. If you are not interested in this individual, it is generally ok to ignore these types of automated messages. However, don't assume an automated message means the individual isn't willing or able to send a more personalized message, it simply means they used the tools the website provided them.

If someone persists in contacting you after you have rejected them, most sites allow you to block members.

#9 For Your Own Safety

If you are brand new to online dating, be aware that some of the profiles you see may not be real people or at least not the people they say they are. Fake profiles exist even on some of the best-maintained sites.

What do these profiles look like? Some appear to be very attractive women who look much younger than their stated age. In others instances, their age may suit their photo, but they are very young and attractive women. Sure young women sometimes like older men and some older women do look much younger than expected, but it's wise to be a bit wary.

  • Don't give out too much personal information (phone number, address, email etc.) until you know you are dealing with a real person.
  • Watch for poor language skills, limited response to questions you ask, and requests for your personal information immediately upon contact. In addition, you may find that the scammer uses the same verbiage repeatedly rather than responding to your conversation in a typical manner.
  • Sob stories or tragic figures are also common. Widowed, horrible events in their lives, an abusive ex, and requests for assistance are sometimes used to gain your sympathy.
  • After communicating online and deeming the communication to be that of a probable "real person", try meeting rather than giving out your personal information. A phisher isn't someone you will meet in real life.
  • While it's not a sure method of detecting scammers, doing an image search on profile images can be useful in discovering scammers. You may find the same photo used on various sites, with a different hometown, different name, different age, etc. Or you may find them listed on websites where scammers are reported. It should be noted, however, that if a profile photo is found on other dating sites and all the information is the same, this individual may simply be using more than one site in order to expand their search.

#10 Move It Into the Real World

You've messaged, chatted, and maybe talked on the phone. You're still at least a little bit interested. Suggest meeting in person. Meet in a public area (it makes it safer for both of you) but not someplace too noisy. Don't make it high pressure, just go for coffee, a drink, or whatever. It's not a big investment of time, it's not a big risk, just do it.

You may or may not have the same level of drive or the need to pursue women as many younger men have, but you'll definitely lose momentum if your potential relationship is stalled in online messaging.

Sometimes "chemistry" doesn't happen over the phone, it happens when you sit across from each other, watch each other's faces, and so forth. That is when you truly engage and experience real interaction.

If meeting her doesn't increase your desire to see this woman, then you've saved yourself some time rather than chatting online for weeks on end. It should be stated though that many very happy and successful relationships don't start with "a bolt of lightning" but rather are a pleasant interaction that you decide to give some time for it to evolve.

Final Words of Wisdom

Don't expect results in a day. When you first join a dating site you will see lots of new people and many will contact you in the coming days. Things taper off over time. There is not a limitless supply of over 50 daters.

You may likely experience a number of "no replies", you may experience a number of people who talk to you a bit and then disappear, and you may encounter others who message a great deal, but never want to meet. This is online dating. Be prepared for it to happen. These people either aren't interested, aren't real, or are the eternal dating site member (the ones who are always looking for the perfect mate, that of course, they never find).

Don't allow your frustration with this to make you decide to quit trying. There aren't that many good dating alternatives out there. Update your profile, your photos, and stay in the game. Over time new people join. Stay positive and avoid the temptation to return to your profile and complain about some of the negative behaviors you have encountered.

© 2018 Ruth Coffee


Ruth Coffee (author) from Zionsville, Indiana on July 18, 2018:

dashingscorpio...absolutely. I've always been about long term relationships and possibly marriage, but to go into it expecting to get married is an attitude that could get you in trouble at any age. I definitely encountered individuals who were going to do ANYTHING to achieve that goal no matter how poor we were as a "match".

dashingscorpio from Chicago on July 18, 2018:

Excellent advice!

I would also add no one should overly emotionally invest in an outcome with any (one individual). Assume everyone online is communicating with multiple prospects much like a company does when receiving multiple resumes from potential candidates to fill a key position.

Everyone has their mate selection process or must haves list.

Attempting to force someone to move at (your) pace may turn them off. Compatibility trumps compromise.

Last but not least I'm always weary of anyone who claims they are "ready to get married" and they don't even have a boyfriend or girlfriend! The "special person" you are with should be the reason why you're suddenly having thoughts about marriage.

Otherwise you're just someone chasing after a {marital status} in search of a "prop". Also people who have marriage as a "goal" are more likely to rush things or ignore "red flags" in order to make it happen. The goal is to marry the right one not the next one!

One has to learn to enjoy the whole dating process and allow a relationship to naturally evolve if it's meant to be.

I along with many other men once shouted from the mountaintop:

"I will never ever get married!": And yet I've been married twice!

George Clooney was probably the most famous "serial monogamist" in the world. He swore he would never ever remarry. And yet after 6 months of dating Amal Alamuddin he proposed.

Life is very unpredictable!

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