Challenges of Dating Apps

I kept my membership to Match.com for a year but my efforts to meet someone gradually slowed down and ultimately stopped after about eight months. I did have several more meetings that were basically like the ones I shared in my blog Match.Com at 80 on my website within the “Widowhood in Later Life” category.

The reason I quit was not only my disappointment with the quality of the men to whom I was being introduced but also the stilted way the introductions and communication were handled by the technology. My response options were limited and not comfortable for me. And the algorithms to identify and enhance communication were bad. The workings of the website did not make sense to me. Of course, there was no way to contact Match.com. about how to use the website or what the various icons meant. Despite my research efforts to understand how to manipulate the website, I found no answers.

Algorithm examples:

Every profile could identify descriptors that would be a dealbreaker for an ideal match. One dealbreaker for me was that the person had to at least have a college degree. (True neither Mark Zuckerberg nor Bill Gates has a college degree. My response to that is that Mark apparently didn’t even graduate from kindergarten because he clearly never learned how to play well with others. As for Bill Gates…there are always exceptions.)

Back to my dealbreaker: I frequently received emails saying, “we have highlights for you!”  Many of these “highlights” had not gone to college! Never mind college, some had not graduated from high school! A “highlight?” Potential “match?” I don’t think so. What was happening? Why did I keep getting dealbreakers? Very frustrating.

Although age was not identified as a dealbreaker, many “highlights” were 20 years younger.  Given that men’s prejudice about women’s looks is still alive and well, what 60ish man would be interested in an 80-year-old woman no matter how good she may look.  Yes, as I have heard, maybe for a “nurse and purse.” How insulting! What a waste of time, energy and enthusiasm for the venture.

I don’t remember if I wrote anything in my profile about distance, but I received many “highlights” who lived 100s of miles away. While it is true the second love of my life may live in a distant state, I don’t remember ever thinking: “Oh if he only lived closer, he seems just right.”

Another point about the “highlights” is that the list I received was not reciprocal. My profile was not sent to the people highlighted for me. The “highlights” were a one-way street! How can they be great for me and not true visa versa? If that’s the case, why bother?

Final algorithm flaw was that if I deleted a person he would reappear as a highlight. It was like wack-a-mole! I could not get rid of him! I guess that was just to give me a momentary false sense of power pressing “delete.” Or was the website telling me “look again”? I was not interested and finally became fed up.

As for managing the site in general, if I received a highlight that looked interesting, I could not always just start a conversation. Sometimes I had to love him (click on the heart), make him a super like (click the star) or delete him (click the X). Ridiculous! People don’t behave that way. Where was the opportunity to respond in a normal human way? There was no option to say, “This is interesting,” or “Do you still study geology?” There was no choice besides loving him or telling him he is a superstar! I gave up.

Knowing that these dating websites are very successful for many—my daughter’s marriage as one example, I decided to give another app a try. I signed up on Silver Singles for people over 50. For some reason I always had to sign in… annoying and the men were similar to the ones I saw on Match.com. I just ignored any bidding from the app for however many months I was enrolled. (Maybe by this time I was in a bad/negative mood.) I felt manipulated.

My last effort was on the app Just for Lunch. Not long after I enrolled, I received a phone call from a private matching company. They informed me that Just for Lunch did not have men in my age range; I had been referred to them. How nice.

The young matchmaker or more aptly, salesperson, informed me that for just $30,000!!!  they would find my true love. I couldn’t believe the amount of money and after many of my “nos” she offered me what in her words was “an incredible deal of just $8000 for three months.” While talking with her—I was curious but not serious—I went to their website and looked at the staff who would be finding my perfect match. I saw women in their 30s with long hair slung over a shoulder almost covering their impressive cleavages. I told her perhaps I was missing a great opportunity but “no thank you.”

I think the successful matches are for those in their 20s and 30s—the tech saavy, not we mature often set-in-our-ways people-oriented oldie but goodies in our 80s.

Relationships—friendships or romantic ones, usually develop through shared experiences—hiking, hobbies, classes, doing tasks, or attending a social event. Conversation flows naturally rather than forcing it. First, talk may be about what drew you to the event/experience. Then conversation typically moves on to other topics such as other interests, books, exercise, activities you enjoy, etc. Common ground evolves and interest in the other begins to develop. This is in stark contrast to immediately ticking off personal goals, accomplishments, wishes, failed relationships etc. All so forced or artificial for a first meeting.

No more apps for me. I’ll think of another way to have interesting, thoughtful, kind, intelligent men in my life.

 

 

17 Comments

  1. Donna M Maria Southworth on October 18, 2025 at 2:06 pm

    This is a beautiful account of how impersonal social media can be…relationships should feel natural…i feel for anyone who is looking for just someone to understand and be with them…it is difficult.

    • Fran Johns on October 24, 2025 at 8:45 pm

      VERY difficult. I live in the city – and have a partner of 30 years I met in a restaurant. I think there may be more opportunities in the city – classes, lectures, museum events, etc. Also I think it’s a numbers game. There just aren’t that many men in their 70s/80s who are healthy and single and smart.

  2. Terry Lineberger on October 24, 2025 at 9:11 pm

    Deborah! I have literally been thinking of you the last couple of weeks and wondering why I had not seen another big post. So happy to get this in my email today! Love your insights and am tuned in to see what your next strategy may be. You go Gurl!! 💪🏻🙏🏻

  3. Judi on October 25, 2025 at 8:00 am

    This resonates so deeply>. While I have not tried the dating apps, it is these experiences of indifference on the part of the algorithms that “match” you and the “why-not-take-a-shot” responses that makes me discouraged about even trying. Thank you, Deborah, for articulating the problems so clearly and vividly for us older persons.

  4. Deb on October 25, 2025 at 10:04 am

    Ha! You hit the nail on the head. Years ago I tried E-harmony at the behest of friends. I winced my way through my profile. It was a very disappointing experience. Very similar experiences. Something in my profile seemed to suggest that I would find bare chested men on their Harley-Davidsons appealing. OMG! If I did find someone remotely interesting, they showed no interest in me. That just made me feel very unappealing. And that was the end of that!

  5. Kathy C on October 25, 2025 at 11:26 am

    I have a happily married friend whose husband is a terrific guy. They met through a mutual hobby but the attraction was initally one way. He liked her a lot but she only saw him as a friend, not in a romantic way. So he WAS a good friend for several years before she realized that as she got to know him, he was really a great guy. Rather than focusing on her previous superficial criteria, she began to realize that what mattered was loyalty, commitment, support, shared interests, etc – boxes that he checked! They finally got married and are living happily ever after. If they had been matched on an app, they would never have had a first date!

    • Eleanor Saslaw on October 25, 2025 at 7:35 pm

      A terrific analysis and summary based on personal experience. I am looking forward to reading the book detailing your adventures!!!!

      • Deborah A. Kahn on October 25, 2025 at 9:38 pm

        Very funny, Eleanor. I am not writing a book, thank you!

  6. Ceil on October 26, 2025 at 12:02 pm

    D, Thanks for your very honest, accurate and hilarious account of trying to cut through the jungle of dating apps. All of it rings so true that I hope the Match people are listening!

    I look forward to more insightful columns in the future!

  7. Jennifer Joffe on October 26, 2025 at 1:16 pm

    What a thoughtful and touching article about the challenges of dating later in life. I especially love the hopeful way you wrapped up the article.

  8. Mary on October 26, 2025 at 2:26 pm

    Thanks for this, Deborah. Some of your observations are laugh-out-loud funny.

    My favorite:
    “It was like wack-a-mole! I could not get rid of him!”

    (Kind of like a restraining order that just will not restrain.)

  9. Meira on October 27, 2025 at 12:04 am

    Fortunately, or unfortunately, I have never tried a dating app, so I loved the concrete (and funny) examples of some of the challenges they pose. Great take on the dating world.

  10. Anne Marie on October 27, 2025 at 12:07 pm

    I just love this! It’s funny yet really honest!

  11. Bonnie G on October 31, 2025 at 7:21 pm

    It seems like this is a great case for staying Fabulous & Single! 😉

  12. Jennifer Anthony on November 10, 2025 at 8:30 pm

    I feel so enlightened reading this post! As someone who married well before dating apps emerged on the scene, I imagined that they’d bring transparency to dating, broaden the pool of possible matches, and remove some of the stress if being set up. You’ve disabused me of all that! Couldn’t agree more that old fashioned social connections are the way to meet people you’d want as a friend.

  13. Judith Bailey on November 17, 2025 at 2:56 pm

    I’ve been a widow for a year and never saw myself as adventurous enough to use Match.com. Now, after reading your account and analysis, I KNOW I won’t ever use it. Still, I have to praise your adventurous spirit for giving it a try. Good work, Deborah!

  14. Marilyn Seiber on November 18, 2025 at 3:08 pm

    As always, I love the photos you put with your blogs. And as usual, you have captured perfectly the discouragement, difficulty, and disappointment these dating apps produce. The totally inappropriate and ridiculous “matches” are laughable if not so maddening. It feels hopeless. So one either continues the search (somehow), gives up, or hopes for a miracle!

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