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6 Musts Baby Boomers Need to Consider When New to Online Dating

By Michelle Hill February 20, 2024 Dating

It seems like at every stage of life we say, “Well, they’re at that age.” Whether it’s teething, or asking why every five seconds, or moodiness, or midlife blues, or reinventing ourselves.

In our 60s, we’re at that age where we often find ourselves newly divorced, newly widowed, or sprouting wings as we continue to fly solo.

Are You Out of the Dating Loop?

As baby boomers, we can wake up one day and find ourselves completely out of the loop when it comes to navigating the online dating world. I was 43 when my husband left, and since I had been married from the age of 20, I had never really dated anyone seriously. I didn’t know how to be single. After a few years when I had emotionally healed, I felt the desire to meet a man and even get married again. Where, I wondered, do I start?

You’re at that age when you may have entered singleness and now, you’re being urged… even pushed… by well-meaning family and friends to get back in the saddle of dating.

How to Successfully Date Using Online Platforms

Only IF you feel ready, here are some helpful tips to get you started in online dating.

Craft a Dynamic, Well-Written Profile

Please have someone else check your spelling and grammar. Nothing is more of a turn-off than poorly written text riddled with spelling errors in a profile. Spel cheque duz knot cache all miss steaks. Let your profile percolate overnight and look at it again with fresh eyes the next day. Be authentic and don’t overshare.

Use a Variety of Photos

Include photos of yourself in several scenarios, including dressy, casual, out in nature, etc. Also, include current pictures, not from 10 years ago when you were fit, trim and wrinkle-free. It’s the same as in a business; under promise, over deliver. And I implore you, please do not take a selfie in your bathroom with the mirror as a backdrop. Smartphone photography is more sophisticated than that!

It’s Time for the Fun Stuff!

Search Profiles

My first suggestion is to set your profile to delete any profiles without pictures. There are too many scammers out there who will bait the “hook” any way they can, and although they can “steal” pictures of good-looking men on the web, in time, you can ask for additional recent photos. Look for well-written profiles. Can they complete an intelligible sentence?

Watch out for the “too good to be trues” as they usually are. If their profile says legally separated, do not go there because their previous door is not closed! Another key point is realizing that not everyone you meet is a potential suitor. Some people you meet may be looking simply for companionship and not a serious dating relationship. I’ve met two lifelong friends of 20+ years on online websites. They weren’t a love connection, but they’ve made wonderful, supportive friends.

Making a First Contact

When you find a person who you think might be a possibility, send a brief note, introducing yourself.

Don’t Tell Your Life Story

If they are sending you kisses or other flirty icons in the first message, watch out because they could simply be seeking a booty call, and this type of man doesn’t improve with age. They could also be an online scammer.

If a man is too aggressive out the starting gate, proceed with caution. If someone contacts you first, and you’re not interested, you’re not obligated to respond. That’s the beauty of online dating. You make it work for YOU! Refrain from giving many details about your life or daily schedule when making initial communication.

Ask the Right Questions and “Listen” Between the Lines

The saying goes, “you don’t know until you ask.” Ask a few questions via the website and only when and if you feel comfortable, exchange personal emails and/or phone numbers. Move at a pace YOU feel comfortable with. Ask broad questions about their lifestyle, interests, etc.

Be ready to answer their questions truthfully but not in full detail. If the conversation is all about them and not a back-and-forth verbal exchange, it’s probably how it’s going to be moving forward.

It’s That Time

The First Meeting

The phone conversations have gone well. You’re feeling more comfortable with this person, and you have some common interests. Time to meet! Suggest a public place and put a time limit on it. You can adjust accordingly if the meeting goes better than expected. Breakfast or lunch works nicely, but I strongly discourage a nighttime meeting for the first date. Ladies, please let a friend or family member know where you’re going – better to err on the side of caution.

Danger, Will Robinson

At this meeting, be mindful of their eye contact and body language. If you sense him mentally undressing you… ding ding… run for the hills… he has one goal… to get into the “PlayStation.” The topic of intimacy should NEVER come up in the first meeting, or even the second meeting.

The first encounter should be a light-hearted, general SHORT story-telling meeting with no talk about financial matters. Just as in your telephone conversations, he should be asking about your life too. A one-sided conversation either way is plain boring.

What I call a one date wonder from many years ago comes to mind. The phone conversations had gone well, and we agreed to meet. We chose a popular burger fast-food restaurant, and this man talked non-stop for two hours. He told me he was an orderly in a mental hospital and had a seven-foot boa constrictor as a pet. As they say, No way, Jose! He was most definitely NOT my prince charming! He did not ask me one question about me or my life. At the end of the two hours (yes, I stayed), he told me how much he enjoyed the conversation… I thought, what conversation? He told me how he felt he could tell me anything. Wow, uh… NO. Buh. Bye.

It’s Your Turn

There you have it. These six tips can get you started toward a wise and successful online dating experience. Yes, there are lots of crazies and cons out there! There are also a lot of super nice people simply seeking companionship.

Use wisdom. Exercise good judgment. Do not proceed if your intuition says something is not right.

Let’s Have a Conversation:

Have you entered the dating world after 60? What has your experience been like? If you’ve met your true love, share your story with us. We will celebrate with you!

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Stephanie Bryant

Legally separated… not true I am legally separated and can’t divorce from another 4+ years as my former husband has a disability and I agreed to keep him on my insurance, so please don’t tell people that. I understand if someone has a question I’m willing to answer and give them the reason. We have not had any sort of relationship for two years prior to the legal separation so I am more than ready to meet someone. As far as showing all kinds of pictures, most guys out there only show their head/ face you lucky if you get anything below the waist.
Everything you said should be on both sides not just the woman. I feel like the guys are not putting the effort forward at all. And any sites I’ve seen you can’t block guys with no photos. If so tell me which one and I’ll join that because everything I put that were dealbreakers like age group, distance, doesn’t matter they get through anyway. I’m done with online dating, even if it means I need to be alone.


I am a 65 y/o professional woman. I am a financial advisor and facilitate workshops for divorcing women. Other panelists include a family law attorney, private detective who is on the state board, therapists and a realtor. Although your tips are good, the success rate of finding a match online is very low.

I think many men have become very lazy about courting a woman. Many people expect immediate chemistry and that is not realistic. If a guy is reasonably attractive(yes, there are some people we will never be attracted to no matter how “nice” they might be), interesting and appears to be mentally and emotionally healthy, I am willing to meet up with them a few times to “see”.

Do not get drawn into endless emails, texts and calls for weeks and months before you meet. In almost every case it will be a let down. The experts encourage you to share a few emails or text and, if you click, graduate to a phone call. A single phone call. The goal of the call should be to SET UP an IN PERSON meet/coffee date. If they cannot talk on the phone and/or are not available to meet for weeks, let them know you would prefer to talk again when they are actually available to MEET. Chances are you will never hear from them again.

I would tell women don’t waste your time communicating with out of state men, unless you are willing to move. Most women do not want to move away from adult children and grandchildren.

If you like someone enough after meeting and you eventually think about taking things to the next level, obtain a background check from a private detective who is licensed in YOUR state. You can check the Secretary of State website. Make certain they have a local tel# and no sanctions. Do not reach out to someone with an 800# as they typically contract out the work. It is worth spend $100 + to make certain the person is not a criminal, not married or living with someone and not broke or in debt. Alot of people play the long game.

Michelle Hill

Love, love, love your comments, Debbie! First, I totally agree in that men have become very lazy about courting a woman. And also, women seem to have become lazy in their approach to men.

Your advice is savvy and timely! With Chat GPT, people can sound much more intelligent than they really are. I also fully agree in the background check if a woman or man thinks a meeting might turn into something more serious.

Thank you for sharing your advice!


Online dating is totally out for. The last time I did that I met a sociopath. It was a dysfunctional disaster.
I’d rather be alone.

Michelle Hill

Julie, that’s so awful that you had that experience! There are a lot of dysfunctional people out there and not just online. We must put values-based guardrails up when we meet new people, no matter where they show up.

I hope you have healed from your online dating disaster.


Unfortunately online dating is mostly unsuccessful in my experience. I am 65, a widower, in good health, and wealthy. Six foot tall, slim. I struggled to get responses from women, no matter how I wrote my profile, and those I did meet were truly awful.  The US Census Bureau estimates that each year, out of every 1,000 widowed men and women ages 65 and older, only 3 women (0.3%) and 17 (1.7%) men remarry (Clarke, 1995). That’s the reality.

Michelle Hill

Hi Gerry,

Hey, I totally get it with how discouraging online dating can be for women AND men. Since I work from home and don’t have a chance to get out much, I haven’t found it to be any better in person. My opinion is that as we age, companionship is more important than marriage; someone to do things with and have conversations with. We can get that from church groups or social groups we may be a part of like a co-ed cooking class, group gym class, or maybe even a travel group.

The reality is indeed stark, but I know love is still happening for people if that’s truly what they seek and they are wise about approaching it.


Mostly good advice but don’t give out your primary email address nor your actual phone number. For email use a free throwaway address that you can ditch If any man becomes a pest. And you should use a burner phone such as Google Voice because if you give your real phone number, anyone can use the internet to find out where you live. I know a woman who was stalked by a guy on a dating site who found out where she lived that way

Michelle Hill


Thank you for your great additions for being careful online! Very on point!!

The Author

Michelle Hill is a Relationship Deception Recovery Mentor specializing in helping women reach healing and wholeness after relationship deception. She is also the author of 5 books, including The Heart Swindler-Reclaim Your Heart and Stop Falling for Liars, Losers, and Lunatics, and two award-winning children’s books.

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