top of page

Ten Questions: One Online Date to Marriage

Couple got married through online dating

Photo courtesy WSJ

 Ten Questions: From a First Date to Marriage

Happy Saturday, all!  This is a monthly column I write with a client answering 10 questions.

  Today, it’s from Debbie*, 66-years-old, an attorney from Palm Beach Gardens, Florida.

  My first Zoom call with Debbie was about 6 months ago in September 2023.  What initially struck me about Debbie was her creativity, kindness and close-knit friends and family that she prioritized. 

  And, she’s getting married in 2 weeks—yes, to a wonderful man she met online.


What was it like to be single after being married?

I was single for 8 years. My ex-husband cheated on me, so I was devastated. Sometimes the ache was physical. It took a while to heal.


What made you decide to call a dating coach?

I had probably been on 100 horrible dates and felt I needed help!


How many dates did you go on in last 5 years and any funny or weird stories?  Did you ever want to give up on dating or online dating? I

I had so many bad dates that I stopped and started online dating many times. I think I mostly attracted married men! I had a surgeon who “forgot” his wallet. That happened more than once. Maybe the worst was the guy who said he liked to dance and play golf. When I got to the meet and greet, he was at least 100 pounds heavier than his photo, and on a walker!

Photo of Debbie and Micahel

Photo of Debbie and Michael (Courtesy of Debbie)


What number date was Michael on Match and how did you end up choosing him as a date?   I don’t know what number date Michael was. Number 2, I think. I loved his photo and his wide range of interests. He is definitely a Renaissance Man! 


Did you know he was the “one” on your first date?  Was there instant chemistry?   Instant chemistry, but frankly it was the conversation that excited me. Of course, the 5-star restaurant, the sport coat, and the roses didn’t hurt! We discussed the other day how we both kept looking at each other during that first date, like, “Is he/she real”?


What Debbie said about 33000 Dates:  Andrea was a big help in writing my profile.  She had me ask my friends and family for adjectives describing me, which was so encouraging.  She also suggested using a professional photographer.  My photo shoot was a blast!  I’m having the photographer do my wedding.




When did you meet him and how long after did, he propose?  When is the wedding?  We met January 11, 2024, and he proposed almost immediately. I assumed he was kidding until one day I just asked if he was serious. That was a couple of weeks ago. The wedding is April 14, 2024. We are not children. I am 66 and he just turned 61. I asked him up front if me being older bothered him and he said not at all.


What did you like about Michael?  Everything! He is kind and smart and loves God. He even loves my dogs. Oh, and he is hot!



Tell us a little bit about common interests/different interests and what you like to do together.  We both have relatively unique interests. He is an actor and a play-write and a contractor by day. I love live theater and reading and I love to renovate houses. He is a really good writer and I like to edit for him. I read lines with him. He is very active renovating my house in his “spare” time. Our interests mesh perfectly! We also have an ongoing Wordle battle!


Did you ever think you’d remarry/find a long-term relationship?    I had pretty much given up on ever marrying again. I am a career professional and used to making my own way. I bought a new house the Sunday before I met Michael on Thursday. The two of us proceeded to gut it! LOL


Tell us about Michael and how the relationship progressed.  When did you know for sure he was the one?  From the first minute, he treated me like I was special. He drove an hour to our date, so I didn’t have to drive very far. He told me his full name and suggested I Google him before we ever even met! That was impressive. We met at a 5-star restaurant. He was dressed well and brought flowers. He knows how to treat a lady. I doubt we’ve watched 3 hours of TV the entire time we’ve known each other. We always find something fun to do or talk about. He went to church with me the Sunday after we met on Thursday. That was incredibly important to me. We talk and we LAUGH, and I mean belly laughs! When he said he wanted to take me dancing, I was a goner! My friends love him. My children love him. We will be married three months after our first date.

Dating Tip?  Don’t give up and hire a pro.



 Love & Laughter,

Photo of Andrea McGinty Dating Coach

Andrea McGinty Founder,

Founder, It's Just Lunch (Sold)

Dating Coach



*Real name of client and photos used per her permission.




Recent Posts

See All



bottom of page