It can take time for people to warm-up during the senior dating cycle. Don’t give up until your gut tells you to or if the thought of kissing the person makes you physically sick.

Senior Dating Planning: Dates 1, 2 and 3

Don’t stress, fantasize or have expectations for dates 1–3, and, if possible, keep the meetings to a public place. Try not to make an emotional investment and share too many personal details. Don’t despair if after the first few dates you are still turned off.

On my first date with my late husband he told me he was divorced and had three children. It wasn’t until date three that he revealed his kids were a set of ten-year-old triplets, and he had partial custody!


I was anxious to marry and have my own family but I really panicked at the possibility of “step-mothering” to triplets!

Catalysts Can Create Chemistry

The most remote simple acts, words, eye contact, smile, expression, can cause you to suddenly “fall into like” or in love. Look for signs of chemistry and compatibility in gestures, words or physical contact.

For boomers, it can be intelligent dinner conversation, sharing common interests, reminiscing about old TV shows and music. The big one is, how do you feel in their presence? Is there comfort and peace?

My friend Donna who is 62-year-old went out with a 60-year-old bank president, Fred, who was shorter and, in her opinion, looked nerdy. I encouraged her to press on because he seemed to be a really grounded, successful and smart man.

Fred came to pick up Donna for a fourth date. She felt instant chemistry as she watched Fred tenderly helping her five-year-old grandson tie his shoe.

The Reveals in Dates 4 and 5

It’s also a good idea to see the person in different environments, scenarios and times of the day. This will offer opportunity to observe more behavior, traits and reactions.

  • By dates 4 and 5 you can exchange more details. Stay charming, warm and sympathetic.
  • Don’t mention marriage or your regrets; reveal medical conditions with caution and restraint.
  • Use discretion on proceeding to sex. Remember this mantra, “Protection Not Infection.” The STD rates are increasing among seniors!

The Hug and the Hand-hold

Non-verbal contact, such as a hug, a handhold or eye-locking can be especially telling. The hug can reveal warmth, sincerity, honesty and chemistry. It also can reveal a physical and spiritual comfort level with that person.

Mary was turned off by Robert’s old car and bad fashion choices. But when he put his arm around her she felt protected and was hooked. It was the first hug on date three that got me. The chemistry with my late husband was undeniable, and I started to ignore my “triplet panic.”

It Was the Dancing!

Vivacious 55-year-old Barbara dated Drew, a successful 70-year-old doctor. They had great conversation and common interests. But even after wining and dining her on dates 1 through 5, he hadn’t won Barbara over.

On date 6 they went dancing, and Barbara was enthralled by Drew’s grace and warmth as well as his dancing skills. Slow dancing can be an instant catalyst as the physical contact can produce a variety of reactions. It’s also a sign of compatibility.

Watch and Wait

Beware and be aware of the instant attraction. It can lead to overlooking faults and a potential bad relationship. After a couple of dates, there may be deal breakers or the initial chemistry may fizzle.

By date 6, you’ve had some physical contact, observed each other in different environments and exchanged personal stories. Even if there is no wild physical chemistry but only compatibility, you may have made a friend. If there’s romance, congrats!

After date 6, I got over my triplet panic as I finally met them. I fell in love with all three kids instantly. My deal breaker on date 3 reversed itself after date 6. Although the marriage was cut short by death, 30 years later I have my own son, a loving relationship with my step-triplets and six beautiful step-grandchildren!

For more dating tips, check out Sylvia’s boomer dating guide and workbook in “Suddenly Single Sylvia.” The guide is based on a team of dating and singles’ experts as well my own personal experience of dating after divorce and loss.

Are you dating in your 50s or 60s? Share your dates 1 to 6 stories. What were deal breakers and/or when and what made you fall “in like” or in love? Do you have any senior dating tips to share? Please join the conversation below!

Angela PageAngela Page is a writer and producer. Her recent release, “Suddenly Single Sylvia,” is a novella and dating guide. In 2015, her award-winning comic romance, “Matched in Heaven,” and short comedy, “Unplugging Aunt Vera,” were released. Angela divides her time between Boca Raton and Los Angeles.

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