Match.com – On Life and Love after 50

A Senior Man’s first-date jitters

On Life and Love after 50 eNewsletter
May 9, 2025
By Columnist Tom Blake

A senior man’s first-date jitters

Bill, a widower in his mid-70s, emailed me for guidance regarding an upcoming first date with a woman he met on Match.com.

I thought it might be interesting, particularly to our women Champs, to know what a man thinks about before and after a first date with a woman.

Bill wrote, “I met an attractive woman on Match.com. She’s 10 years younger. She and I agreed to meet for coffee at a location about halfway between where we live, a two-mile drive for each of us. From her profile picture, she is pretty. I’m a little nervous. Her name is Jackie.

“We talked over the phone and knew at least we had a good conversation before we got together. That is a must for first-date people!”

“Can you give me any advice?”

I replied, “Is this your first date since your wife passed away?”

Bill answered, “No, I’ve had a few dates, but I’m not exactly Joe Stud, you know. But I’d like to impress her.”

I said, “Relax, I can tell you are nervous. But that’s ok, after all, this could become your future mate. Just slow down and calm down.”

“It goes without saying to wear a clean shirt. Smile when you greet her and shake her hand. No hug or kiss when you first approach each other. Men tend to talk too much when they are nervous. Be sure you ask questions about her. Encourage her to talk. Make direct eye contact with her. Smile. Use first-date etiquette; actually, any date etiquette.”

Bill said, “Thanks, that will help me break the ice. I will talk for no more than 40 percent of the time and ask her questions. Her profile says she still works full time. I will let you know how it goes.”

A few days later, after his first date, Bill sent me an update. “It went okay with Jackie. She is pretty. Will we see each other again? Probably. It could happen, but I’m unsure. Frankly, it wasn’t a great connection. She didn’t ask me many questions. I’m 6’ 1; she’s 5’6”—so that works for me. Not too tall and not too short.

“You kind of know if a woman is very interested, somewhat interested or not interested in you. She is somewhat only. But who knows for sure?

“She is divorced and didn’t talk about her ex at all. When I mentioned my wife, this woman sort of felt bad but had no questions about me. When I talked about my interests, the conversation didn’t go very far, but we stayed with her interests and travels.

“It possibly could go somewhere, but I didn’t think she appreciated the breakfast sandwich and beverage because I would have liked a nice thank you for my effort (liked she kind of expected me to pay and I guess that’s ok.)

“She steered away from future plans. I didn’t ask if she wanted to get together again or make any future plans.

“We didn’t get into politics and talked about schools, kids and travel. I probably could have gotten a little more personal and asked what she thought of me. But I don’t want any rejection. We talked for over an hour, so it was going ok, but probably not a strong connection.

“So where does this go? I’m not sure and I’m not clear about my feelings. I could reach out again, but I may leave the ball in her court for her to reach out to me if she is interested enough. So maybe I will ghost her or send her a text in a week to see how she is doing.

“I mentioned a few ideas about walking together on a hike near the beach or something and got no response on any idea she might have to do something. So, no, the date success wasn’t 100%, but more like 35%.

“At the end, I gave her a small hug, but she wasn’t responsive. So, it left me thinking, ‘Do I want to pursue her anymore?’ Maybe there would be too much work involved. She still works and seems busy. Perhaps some of my thoughts may help her. I want some kind of gratification or some kind of future interest to make me think that she and I want a relationship.

“Oh yes, I said at the very end, ‘Do you prefer a text or a call? She said ‘either.’ So, she could be still in it, but not who knows? Maybe it’s me because of my feelings. I don’t need to start chasing or try to create a fun experience. I see myself spending money on dinners and maybe going nowhere.”

Tom’s Comment: So that’s how a nice gentleman feels. If there’s any message in Bill’s story for women, it’s that if you like a guy like Bill on a first date, be a little more assertive, showing affection like a kiss on the cheek and saying, “Let’s get together again.” And ask him more questions. However, what Jackie did may indicate that she doesn’t want to proceed seeing him and didn’t want to hurt his feelings.

Senior dating sure has its challenges.

Senior online dating in Palm Springs

On Life and Love after 50 eNewsletter Apil 21, 2023

By Senior Dating Columnist Tom Blake

Editor’s note: there are three parts to today’s eNewsletter

Part 1 – Senior Online Dating in Palm Springs

I’ve been staying at my Palm Springs vacation home for nearly two weeks. I hesitated to mention in recent eNewsletters that I was going to be in Palm Springs because I have four friends who read the columns and who live in the area. They might wonder why I didn’t contact them on this short visit.

The answer is simple. I’ve had several home maintenance items to tackle before my next tenant arrives in a week. That tenant will be at my home for only two weeks and then I will return to PS and contact my buddies who live out here at that time.

Also, I knew I’d be occupied with trying to meet some local women online. Being out here without Greta for the first time in five years is brutally lonely. Meeting some new people helps ease the pain and can give one hope. Many people online are in a similar situation. They have lost their mates also; so, many of us have that in common who are using online dating sites, and yet we are still grieving.

I wondered if my initial month-long senior online dating effort which had previously focused on my Dana Point zip code perimeter of 25 miles was wasted by my coming to Palm Springs. The answer is no. I’ve met some wonderful women in the Dana Point area. Just no lasting connection yet.

But I wondered how would I meet women within a 35-mile radius of Palm Springs while staying out here.

I learned that it’s very simple to search the Coachella Valley area by just switching to my Palm Springs zip code on both Match.com and Zoosk dating site, the two sites I use. Presto, women within a half-hour drive and closer suddenly appeared. Besides them living in Palm Springs, other cities pop up such as Palm Desert, Rancho Mirage, La Quinta, Cathedral City, Indian Wells, Indio, and even Beaumont and Banning. It’s been an adventure and learning experience for me.

Women in the Coachella Valley are extremely talented. They play pickle ball, golf, swim, do water aerobics, paint, hike, and ride horses.

Part 2 – Painting benches and picnic tables for the city of Palm Springs

This past Saturday, while on Match.com, I was chatting with a Palm Springs realtor. She asked where I attended college. I said The University of Michigan. The realtor said she knows a woman named Diane Morgan in Palm Springs who also graduated from The University of Michigan and is a talented painter and has worked on some painting projects for the city of Palm Springs.

The realtor said Diane was having a bench she painted in Demuth Park Palm Springs, an expansive park in the heart of Palm Springs, dedicated that very evening and suggested I go see it and say hello to Diane.

I had nothing to do so I went to Demuth Park and met Diane there. We had time to chat. Her freshly painted bench with the Hummingbird on it was dedicated to the city that night, is pictured above. Diane said she was told the Mayor would show up and say a few words about the new bench. I didn’t stick around for that.

The point of this story is that positive things can happen when seniors use online dating sites. The people you connect with might not be a match, but they might know of other people who could be.

And those other people might not be online. Diane wasn’t online, but she was great for me to meet.

Diane also mentioned she had been commissioned by the city of Palm Springs in the past to paint two benches on Palm Canyon Drive, near the famous Sonny Bono statue (many Champs have sent pictures of themselves posing with the Sonny statue). One bench is 10 yards south of the statue and the other one is across the street from that first bench in front of the Birkenstock Store. The latter bench is dedicated to “Saving the Bees.” (Photo below by me).

In addition, Diane mentioned that she hired the artist who designed a unique fountain called The Rainmaker, which is located at the intersection of North Palm Canyon Drive and Alejo Road, a couple of blocks north of Diane’s benches.

OK, OK, I know you Champs are wondering, was there a relationship connection with Diane? No, but Diane and I became friends; she’s already in a relationship. However, It was the experience of meeting an interesting new person that was so enriching.

One thing that made me chuckle about senior online dating hair color. I’ve usually dated brunettes. And then I realized that the women aged 65+ on Match.com and Zoosk are almost all blondes. I’m guessing that blonde hair more easily covers the gray hair most of us have as we age. Some, of course, show their true gray hair. I might want to take a lesson from them regarding my ultra-white hair. At 80+, it is what it is.

Another thing that brings a smile is the unique name some women post to their profile on the front page. Here are a few examples:

BabyGrand – Why? She owns and plays a Baby Grand piano.

AlwaysBhappySim – She claims to be the world’s best parallel car parker.

CheerfullyTough – I guess her name means don’t mess with her.

Aaliwood,71 – Perhaps she spends her off season in Hollywood.

BJZ,76 – Anyone’s guess.

Papillion, 73–Is she seeking Steve McQueen or Dustin Hoffman from the Papillon movie?

TuscanyDawn – She must love Italy, at least in the morning.

Carpe diem, 73 – She must like seizing the day.

Part 3 – Champ Jane decides to begin online dating after 15 years

Champ Jane emailed this week, “Thank you for your newsletter. I have been reading it for a long time. I even came to one of your singles nights at Tutor and Spunky’s Deli in Dana Point many years ago. I now live in Eugene, Oregon.

“I have not done any online dating for at least 15 years. But I’m ready to put that toe in the water again. So, I have really enjoyed the current online-dating thread in your eNewsletter. Tips and all.

“I find it very odd when women say they will only date a man taller than them. My sister has been married to one of my favorite men in the entire world for 50 years. They have an incredibly wonderful relationship. He is at least two inches shorter than her. How much they would have both missed if something like height had kept them from that initial date.

Height-wise, I am 5’8”. I have dated two men who were shorter than I am. Truthfully, it kind of turns me on when a shorter man flirts with me. It makes me think he has a healthy self-image.

“I am in Southern California and will be back in Oregon at the end of May. That is when I will post my profile.

Tom’s question: “Jane, What made you decide to put your toe into the dating water again after 15 years?”

Jane replied: “I had two short-term relationships with two very nice men, but the connection wasn’t there. Plus, I have dated a bit here and there. Then there was Covid.

“And then on Labor Day, 2020, my house and all my possessions perished in a fire. That was sobering.

“I purchased a home that needed a lot of work. Much more than I thought. That was also sobering.

“I am trying to make a new life in Eugene. I do love the thought of a companion. But the difference is that now I feel worthy of a relationship. I feel that I have a lot to give. However, it must be the right person. What that means is someone I’m attracted to; someone I can laugh with. Someone caring and kind.

“Meanwhile, I’m doing some art, taking classes, and getting my dancing shoes out of the closet (now that venues are open to dance again). I’m trying to get out in nature, and I am enjoying my life.

“I now don’t feel at all desperate. I have a very full life. If I find that certain someone, it will be the icing on the cake. So, here is to living life at its fullest and remaining grateful for my blessings.”

Thanks, Champs. It would be rewarding to hear why other Champs have also decided to resume senior online dating. Fill us in.

Match.com brings a senior couple together

On Life and Love After 50 eNewsletter

April 1, 2022 eNewsletter #13

by Tom Blake

Terri, 71, Palmdale, California, was one of the 16 Champs included in last week’s eNewsletter. She mentioned that she had recently met a new man who is a great travel partner. I asked if she’d share with us how they met and for more details about their evolving relationship. I told Terri she looked about 40 years old in her picture.

Terri said, “I‘ve always taken good care of myself. I guess I didn’t do too bad in the ‘picking good parents’ derby, either: My mother, a tall, gorgeous redhead, worked as Rita Hayworth’s double at Columbia Studios in the 1940s. She turned heads well into her 70s when she was running for a seat on the Lancaster City Council.

“My father was nearly 6’3” (very tall for that generation) and an imposing figure as well. He was a pioneer in the serve-yourself gasoline business in Los Angeles and “Big John” had the dashing good looks of a George Brent or a Don Ameche. They were a tough act to follow. Thankfully I’ve managed to have an interesting life on my own!

“I met Rob on Match.com, back in the dark ages of 2021, right in the middle of Covid-19, and right after we had both received our second vaccines in February 2021. I guess we were feeling a little invincible.

“He lives in Atascadero and I was considering a move to Paso Robles, near that area, so I put that zip code in a Match.com search to see what the dating pool from age 66-76 might look like. Rob had been widowed for about a year after a very long marriage. His daughter had suggested he give Match a try. He was on there for about a month. I was divorced in 2014 after a 33-year marriage. I was on Match a lot longer than I’d like to admit, however, I met some interesting men and some who remain, dear friends, today.

“I saw but didn’t answer Rob’s profile, thinking it deserved more than a cursory or flippant reply. Surprise, surprise, he then wrote to me, giving his email address and asking if I’d like to begin a conversation? So, I wrote him back.

“We talked on the phone for a couple of weeks and then he invited me to a family barbecue at his house. He sent me a dozen red roses before the BBQ. And it really was a family barbecue: his daughter, her boyfriend, his grandson, his best friend, and her boyfriend. I guess it was the ‘approval committee’ barbecue and I passed!

“We’ve been having fun ever since and I have been thankful for his presence in my life throughout some health problems I encountered (since recovered). My life would have been a lot tougher this past year without Rob’s positivity and his presence. Now it’s time for us to travel some and to have more fun. Life is an adventure!

“Rob owns a nice home where he lives with his daughter and grandson. So, we’ll be something like an LTS (living together separately) couple about 15 minutes away from each other.

“Rob was born and raised in Australia. He enlisted in the Royal Australian Navy at 16 and traveled the world for 20 years, including extensive service in Vietnam. Upon his retirement from the Navy, he was a ranking officer. He helps his fellow RAN (Royal Australian Navy) officers celebrate ANZAC day each year (see Rob’s photo).

“After his military retirement, he lived a dozen years in England and six years in France, working as an antique dealer. His American wife wanted to return to the US, which brought them to California, and the Central Coast where he has lived for the past 24 years. Kind of an International guy, no? Love that Aussie accent, and Rob’s a great travel partner!

“He’s an honest and up-front guy, with a high energy level to boot! I would say that persistence and resilience are two of the best qualities one can possess if you want to meet someone and pursue that through dating sites. “Thanks for your columns, Tom, and for all I’ve learned from you about life and being a ‘senior single’ in the past 7+ years!”

Part 2
RETA – “No Grumping for me”

Reta, 84, Cincinnati, emailed: “No Grumping for me. After reading all the comments from the ‘young champs,’ I had to comment on my situation. I’m 84 and babysit my three great-grandkids ages 2,4, and 6 three days a week. This is when I notice fewer aches and pains and enjoy life. Sometimes I’m driving the 30-minute drive home after dark-not a problem.

“I also volunteer to crochet shawls for a hospital. I have different groups of friends to keep in contact with. I don’t walk as easily as I used to, but I keep walking and keep doing. Tell that grumpy man that he needs to do the same.”

Tom’s response to Reta, “Good on ya! I like your comment about being around the great-grandkids helping to keep you thinking young. And driving after dark? Courageous. And volunteering. You’ve got all the healthy buttons pushed. “Proud of you. Keep it up!”

Senior Meet and Greet in Dana Point

Tom talking to seniors at Dana Point California Meet and Greet May 22 2019

On Life and Love after 50 eNewsletter – May 31, 2019 – Keeping me focused – The next Senior Meet and Greet in Dana Point California is Thursday, June 27, 2019

by columnist Tom Blake

Get it right, Tom

I received several comments about the singles Meet and Greet recap in last week’s eNewsletter. However, the most frequent comment wasn’t about THAT Meet and Greet, it was about the NEXT Meet and Greet. I wrote it would be Thursday, June 28.

About 20 Champs set me straight (in a cordial and respectful way). In 2019, there won’t be a Thursday, June 28. That Thursday is June 27. I stand humbly corrected.

And speaking of Meet and Greets, Randall emailed, “Tom, I’ve been advised that you have a singles group that meets at Tutor and Spunky’s Deli in Dana Point on a monthly basis. I know your reputation for being honest and would like to attend the next meeting.”

My response to Randy: “With this group of astute Champs, anything less than honesty would be exposed in a nanosecond.

“The May Meet and Greet at Tutor & Spunky’s Deli was the first one since I sold the deli in 2015. Turnout was great, about 100. We will continue to have them as long as senior singles in our area want them.”

I suggested Randy sign up for this On Life and Love after 50 eNewsletter on FindingLoveafter50.com, so he can be updated on upcoming events and singles information that I consider important, interesting (and honest!).

Romance Scam alert

Randy’s “being honest” comment leads me into a story of someone who wasn’t honest. I’m sharing it today because I never want any of our Champs to be scammed out of money, assets, self-respect, or anything.

I read an article written by Faith Karimi that appeared on CNN on May 24. A woman from Georgia was swindled out of $80,000 by a young scammer. I couldn’t determine from the article the age of the woman but was shocked that she was so naïve and foolish that she gave the man the money after one week of dating.

Here are some of the excerpts from the CNN.com article:

“John Martin Hill, 35, connected with the woman…on Match.com in late March…Hill took the woman out on a date the same day they met (online), and the two agreed to get married a week later… (I thought to myself—you must be kidding–she met him in person on the same day first contact was made, without checking him out, and, agreed to marry him in a week?).

“He told the woman he’s a millionaire, and they decided to invest in a love nest. The woman gave her now fiancé $80,000 (cash) to help with the home’s purchase…

“During their short romance, he convinced her that they were in love and wanted to buy a house together…When he got the money, he cut all contact with the woman… (shocking, I know).

“The man lived with another woman and a child in Duluth, Georgia — and he’s wanted in Virginia, Delaware, Maryland and New Jersey for similar scams, authorities said.

“Since then, several women have come forward and said they were in a relationship with him, or, knew women who were. Hill has changed his name at least five times in two and a half years, police said.

“Police arrested him Wednesday at a hotel in Franklin, Tennessee…”

The CNN story also stated, “’By sharing this story, it is our hope that he is not able to victimize any other women using this scam,’ Gwinnett County Police said in a statement. ‘These types of con men are very good at manipulating their victims. They tend to say everything that a woman wants to hear.’”

Emphasis on sentence above: they tend to say everything a woman wants to hear.

Apparently, Hill has used several aliases including Gregory Hill and has scammed women in several states. He’s behind bars now, and it seems he will be for years to come. He was busted in 2012 but was still able to operate scams since then.

How anyone could be so naïve is beyond comprehension. However, it happened to women in several states. Wow.

Link to that article:

https://www.cnn.com/2019/05/24/us/georgia-alleged-romance-con-artist-trnd/

In fairness to Match.com…

I don’t want to give the impression that all Internet dating sites are bad, and I’m not singling out Match.com. I am merely re-emphasizing that one must be careful when meeting strangers online or anywhere.

This week, Don, one of our Champs, wrote to say he would attend the next Meet and Greet. Don said, “I met the perfect lady for me on Match.com a little over a year ago and she seems to think I am the perfect man for her. Edie is 73 and I am 78 and we are doing great.”

Meetup.com is not a dating site, but here’s why it’s a good option for meeting people…

Vicki wrote, “I’m 70. Widowed 5 years. I loved being married and though I don’t want marriage at my age, I do want a companion. I’ve been lucky and I’ve dated a lot.

“I’m a determined lady and I’ve used all the dating sites (and I took dating seriously) and I’ve had horror stories, but I’ve also met some ‘ok men,’ just never ‘my man.’ I always picked men that were 3 or 4 years younger; I’m an on-the-go, fun, lady who attracts younger men, men who also like to get out and have fun).

“I’ve always turned down dates from anyone younger than 3 or 4 years. Even though I’ve always been told I do not look my age, I never strayed from that age range because I was brought up that women date their age or older.

“As for the you-look-younger line I hear, people say that to be nice and your age is going to come up sooner than later when you date, and I’m a bad liar. I always told the truth about my age and ignored the invites from the 50s + group.

“I joined a fun Meetup.com group–single and 55+ was the requirement. I recommend Meetup.com to meet men vs. online dating. Of course, more women than men are in this group, but lucky me, an attractive man 10-years-younger, took a liking to me.

“We went out, he knew my age, he didn’t care! I wrestled with the age differences until I realized how much fun I was having with him, and guess what? We are now companions, spend at least 4 or 5 nights a week together, have gone on two trips and I’m happier than I’ve ever been in a relationship!

“My new advice for all daters over 55 is just go for it, enjoy every minute you have and forget age, be honest and if they don’t care, you don’t care! You are as young as you feel and when anyone asks my age I now say, ‘I’m old enough to know better than to answer that, and young enough not to care that you asked!’ Then I wink! It usually gets a laugh!”

Memorial Day Ceremony and Flower Drop at the Palm Springs Air Museum…

A P-51 Mustang participated in the Flower Drop flyover. This plane was flown by the Tuskegee Air Men

Greta and I were in Palm Springs on Memorial Day. We decided to attend the 22nd Annual Flower Drop & Air Fair at the Palm Springs Air Museum, known as one of the best air museums in the world. As a Navy veteran, Memorial Day means a lot to me. I wrote about our incredible day there, and included several pictures and videos. If interested, go to http://www.TravelAfter55.com. The home page will open on the story. That is the same website with all of our travel adventures on it.

Reminder: The next Meet and Greet is Thursday, June 27, 2019, at Tutor and Spunky’s Deli, 34085 Pacific Coast Highway, Dana Point, CA. 5 to 7 p.m.