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SAFE Online Dating for Mature Beginners

Wendy C. Kasten, Ph.D.

I met my husband online. Most of the couples I know over the past decade have met on online dating sites. It is the dominant vehicle of our times for finding partners.

The site, Ok, was free (at the time), and it started by having each member state what they were looking for (ex. I am a man looking for a woman) then answer a long list of questions. Some questions were of a serious nature, such as political affiliation and religion and beliefs, while others were silly, such as if you preferred Coke or Pepsi. But, the point is, that it is possible to know a great deal about a person before moving toward meeting each other.

I have viewed online dating as an opportunity to get to know a person from the inside out, rather than from a brief meeting.  For online dating, you still have the benefit of a photograph but not an immediate in-person meeting.

You probably have heard of individuals who have been scammed through online dating sites. The potential is real. Before I discuss the particulars of online dating, I will share the possibilities of a scam to help you recognize one right away. Then, I make recommendations of what to do before you agree to meet someone in person, how and where you agree to meet, and what happens next.

SCAMS and Staying Safe

A good friend assured me there is a large office building in an African country where many people go to work every day, and their job is to dream up scams to get money out of people. One deputy sheriff told me the Caribbean is another scam hub, and there may be others.

The first of the two times I taught about this topic at Belfast Senior College, then Sheriff Jeff Trafton (since retired) co-taught the class to address scamming. Next, I share the major points we covered. 

All scams have one thing in common. That is money. Anytime you are in a position of talking to someone you have never met or met briefly, and you are asked for money, it’s ALWAYS a scam. No exceptions. Remember this above all else. Even if you feel you know them through conversations or emails, it is a scam. Even if you think the person has been really nice, or, if you think you care for the person, or the person claims to care for you, it is a scam. If there is a money request, STOP. Block all communication. Feel bad or sad or disappointed and move on. Resolve that you learned a lesson, and you are smarter because of it.

If you send money, you will never get it back, no matter what they say. No exceptions.

A second important point that nearly all scams have in common is a sense of urgency. Someone you are talking to needs the money for something right away. You get pressured. They promise to pay you back. Yeah, right. Again, STOP. Block further communication. Feel disappointed, eat ice cream (or whatever) and move on, wiser than before.

         One thing to look for as well is that many scams originate in foreign countries. Pay attention when you see any errors in English grammar or spelling. Second language speakers are rarely perfect in their English.

         Catfishing is the term given to the scamming practice of a person using a fake picture and identity, then endearing him or herself to a man or woman with lovely talk and many promises, when the real intent is getting money. The person supplies a picture of someone else, a fake profile, and their skill at their scam can make an intelligent person believe they are lucky and have found true love, when they are simply being victimized by someone, usually overseas. Charlene, a friend, came close to getting caught in one such scheme. Fortunately, bells went off in her head when her potential match requested a great deal of money from her. In previewing this article her reaction was to remember what her father often told her – Anything “which seems too good to be true” is something to walk away from.

         Here are other common red flags:

  • Your potential person-of-interest cannot meet you in person because:
  • They work far away.
  • They work on an offshore oil rig.
  • They travel a great deal for business.
  • They live in a foreign country.
  • You catch your person-of-interest telling you a little lie. You may decide it’s no big deal. But IT IS. Where there is one lie, there are always more.
  • When you finally talk about meeting, they are never available on weekends (That may mean they are married and looking for someone on the side).
  • Someone declares they are “in love” and it seems too soon.
  • Someone acknowledges that they have a partner, but it doesn’t count because their partner is disabled (what sort of person goes on dates when they have a disabled partner?).

So, You Join a Dating Site

There are lots of dating sites out there. They specialize in people who are younger, older, have a religious focus, are environmentally conscious, or are looking for encounters with no attachments, etc. Most sites deal with heterosexual and other kinds of relationships. You will be asked early on to acknowledge your gender and what gender you are interested in pursuing.

 close-up of hands holding each other

Here are some important points to look for in a dating site:

  • Price. Some are free and others charge. If the site is free, it would be unlikely that members are vetted, as background checks cost money. Find out what age groups they best serve.
  • Cancelation. I would never join anything that charges a monthly fee unless I also knew the cancelation policy, and how one gets in touch with customer service. And perhaps, seek reviews on the site’s customer service record.
  • Profiles. Every site has templates about how to create your profile. There may or may not be questions (I am a fan of questions). You will be asked to write a profile. Think in advance about writing a short biography including your interests, must haves, deal breakers, and what you are looking for (Marriage? Dating only? Undecided?). When reading profiles of a person-of-interest, avoid profiles where the person only talks about how wonderful they are, with little or no helpful information (such as “I really know how to please a woman,” and as you might guess, the profiler is talking about sex, when some women would say the real way to please a woman is to clean her garage). Here are some profile tips:
  • Introduce yourself – gender, age, marital status, perhaps mention your current or former profession (retired doctor, retired teacher, retired emergency responder, etc.).
  • Affirm you are unmarried and unattached (in other words, no current love interest).
  • Since everyone reading this is probably a senior, you need to say if you are active and healthy or in a wheel chair, or needing oxygen, etc.
  • State your most important interests, such as bowling, gardening, fishing, traveling, etc. (I used to state I would not date anyone without a current passport)!
  • You might share what others say about you or how friends describe you.
  • State what you would not tolerate. For example, if you were a non-smoker, would you tolerate a smoker? Someone from a different religion? Different political view?
  • Do you have deal breakers? For example, would you not consider moving from your current home? Would you relocate to another state?
  • Share whether or not you have children and/or grandchildren (after all, if you get involved, this person would meet them).
  • What is your status with pets? Do you have a dog? Allergic to all of them?
  • Most profiles require a photo. It should be recent. It should be honest (not before you gained 50 pounds). You can have a friend take it with a smart phone. There will be a place for you to upload that picture.
  • Anonymous Communication. Most sites offer a way to communicate within the site. You can often do this for quite a while. This way, you know things before you share personal contact information. 

You’ve Met Someone Interesting on the Site

         These next steps are very important, and are the most critical to staying safe. This is assuming the site does not do background checks of its members (and most do not).

         Exchange many emails. If you believe you are getting valid information that someone on the other end took time to write, it is one sign that they care about you as a potential person-of-interest. Don’t accept short answers, someone saying “we can talk about that when we meet,” inconsistencies, or anything that does not seem quite right. 

         Vetting. This is especially important for women reading this. Most gentlemen will be willing to give you their real name and their actual address. With this information, do the following.

  • Google their name. Not everyone has an online presence, but most people do.
  • Put their name in on Facebook. If you don’t use Facebook, ask a friend or son or daughter to do this for you.
  • Go to Google Earth. Insert their address. Find out if the address is real. If it is an actual address, Google Earth will show you an aerial photo of the home (one friend did this and learned the address the person gave her didn’t even exist).
  • Ask the county where the person-of-interest lives and where they lived before. Go to the county website and the “Clerk of Courts.” Put in their name. Recent court records will show up including divorces, arrests, sentences, etc.
  • If you have any concerns about communication you have received from someone, consider reaching out to local law enforcement. They are eager to protect their citizens from scams. They may recognize a pattern you missed that is a current popular scam.
  • If you want more information and you decide it’s worth it, you will find many places online that will do more checking on a person, supplying family member names, past addresses, etc. Costs vary but are typically around $75.

You Think You Would Like to Take Some Next Steps

         IF everything seems good so far, and you have NO concerns, here is what you can do next. Do NOT skip this step.

         Have several regular old-fashioned phone conversations.  Using your cellphone (because if needed, it’s easy to block someone). I would advise at least three phone conversations. Did you two find lots to talk about? If the conversation is boring on the phone, it probably will bore you in person.

         If you think the phone conversations went well, and you felt good about them, schedule a video call. This is easy nowadays. On an iPhone you can use Face Time. If you use Facebook, you have Messenger. There’s a popular app called What’s App? That has video capabilities. Zoom accounts are free if you only talk for a limited amount of time.

         These are sources where you find out if the picture on the dating site is the same person, if that picture was more or less up-to-date, and if you enjoy the person’s looks. Chemistry matters even when we are older.  Have at LEAST one conversation where you genuinely feel you enjoyed it before deciding to move on.

         The Coffee Date. You have decided to meet. Here are a few rules. They are very important. No cheating.

  • First, dates are for coffee, a drink, an ice cream, or a walk in a very public place. Not lunch. Not dinner. Meals can feel very long if things are not going well. 
  • You must make it finite (like maybe an hour or less, because you have an appointment afterwards).
  • Use your own transportation. Don’t let anyone pick you up at your home.
  • You must tell someone you trust where you are going and what time. Have that person call you during the date. Excuse yourself to take the “important” call. Let them know if things are going well. Your “out” if they aren’t, is that the person has an urgent need and you must go and help them.
  • If the person-of-interest asks you then and there if you would like to get together again (which is awkward), only say yes if you feel certain. Otherwise, say, “let’s talk later on the phone when we have each had time to think about it.”
  • How do you FEEL after the visit? If you don’t feel like you had a good time, don’t go again. 
  • What do you say to the other person if they want to get together, and you do not? You can say it was enjoyable meeting them, but that you don’t believe the two of you are a good match. Match is an important no-fault response.

You Want to Move Forward

         Getting to this point is very exciting. You may feel sixteen again (except maybe for your aching joints). Just a few tips here.

  • Be careful of having too many expectations too soon. I once read that women assume when they begin dating someone, the relationship is exclusive, and men do not. Don’t assume. Do talk.
  • Intimacy. In our American culture, there is sort of an expectation of intimacy after several dates. If you aren’t feeling it, don’t have a third date. If you need more time, initiate a conversation about this.


         One reason I taught the Online Dating for Mature Beginners class a second time for Belfast Senior College, is because on an evening walk, I ran into a woman from the first class. She was with a guy, holding hands, and beaming. She recognized me, and declared her success, and encouraged me to teach the class again. So, I did.

         Don’t expect immediate results. Don’t take rejection personally. If someone rejects you, they were clearly not the right person. You can like and appreciate someone and not be a “good match.” In other words, someone might not be a potential long-term partner, but might become a good friend. One of my best friends still, today, after many years, is a man I met on a dating site. We both highly appreciated each other and still do. However, there was zero attraction. I think of him like another brother.

         Also, don’t give up too easily. This is a big thing. It will take time. I lost count of how many dating sites I tried before I found my husband and how long I looked. The act of looking can be fun. Like a little hobby. And it takes time to do it well.

         Please enjoy the journey if you decide to try it. Be open to different kinds of outcomes (Perhaps, a person will become a good friend. I even found a terrific accountant!) As long as you are very careful, this could be fun.

More Dating Tips from Experience

  • Older folks are like package deals. You get what you see. Are you okay with the way the person is?
  • Older folks are set in their ways. Are you willing to make some changes? Is your person-of-interest willing to change their life? (I once had a date with a guy who invited me to dinner at his home where he’d just moved in, and he stated up front that he would live there for the rest of his life. Hmm. He wasn’t open to negotiation on changes).
  • Would you relocate to another town or state for the right relationship? It’s a good idea to think about this.
  • Is your personof-interest relationship material? Once I asked a single colleague what she was looking for in a relationship. This person responded what her ideal date should look like, how tall he should be, what body type, and that he should be athletic (nothing about relationship qualities). Another friend held out looking for her ideal guy who she was convinced would be a certain height, blue eyes, and even what his first name would be because a “psychic woman” told her that’s what would happen. It didn’t. Hopefully, you have thought about qualities you are looking for in a partner, the inside stuff that matters, such as attitudes, caring, flexibility, and honesty.
  • Is the personof-interest in reasonable health? Some older folks are looking for someone to take care of them in their old age. Is that okay with you? In a good relationship, hopefully you will be taking care of each other, with health always being a wild card. Give this issue some thought.
  • Be careful talking about your last spouse. Of course, you will share that you are widowed or divorced, and maybe a few other major things (how long ago these things happened, that it was difficult, etc.) But what you should NOT do is spend a date ranting about your ex or pouring out your grief. Nor should you memorialize your deceased spouse on a date.
  • As things progress, are you beginning to meet the family of your date? While there may be legitimate reasons you cannot meet their family (such as they live in Australia), if months or a year go by and you’ve met no one, there may be a reason, and it’s not a good sign. Ashamed of you? Afraid of family reaction? Hiding something?
  • If only one of you has children. Lots of times, this isn’t a problem. But sometimes a potential partner is so into their kids, and the needs of their kids, and indulging their kids, ensuring an inheritance for their kids – where you find yourself wondering where you fit in. Will you ever be a priority?
  • If both of you have children. How will holidays, like Thanksgiving, be carried out? How will inheritance work? Especially if you acquire assets together.
  • If one of you owns a house. Would you be comfortable living in a house you don’t own or co-own? For some people this is a problem, and others don’t care.
  • If the personof-interest was never married or in any long-term relationship. There may be some good reasons someone never married. However, some of those reasons may not be good. So, be sure to learn more.
  • Widowed people know about marriage. A man or woman who had a good marriage may be a good candidate for a second one if they are ready to move on.
  • If you decide to meet someone far away from home. Make sure you travel on your own dime and arrange for you your own hotel room. Have an exit plan in case you need it. 
  • Money. You must talk about it. You must not cohabitate without an agreement. It should be fair and equitable with the resources from each of you. These conversations need to be honest and open, even when they might be uncomfortable.

The following link provides questions are good to think about: (Thanks, Oprah).

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