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10 Dating Questions with a Client: Allie

photo of allie


Welcome back to my 10 Questions column. A little background: Allie, 58 years old, became my client in February 2024 and the first thing I noticed about her on our Zoom call was her outgoing, upbeat personality. Yes, she was excited but also nervous as she had never done online dating.


She was married for 17 years, divorced for 5 years, with two children in their 20’s.  She’s an executive in the fashion industry in New York/New Jersey.  Allie also had interesting photos:  coming from fashion and arts, one showed her at work and several others at museums around interesting sculptures.  They were unique, colorful, and eye-catching.



1. What was it like to be single after being married?

 Being single after being married with kids was like entering ominous uncharted waters without a life vest - I was uncomfortable and insecure, especially with the scary future thought of dating “online”, so I filled all of my time with my kids, work and more work.


2. What made you decide to call a dating coach?

After a very long time of “all work, no play”, I decided it was time to reacquaint myself with my younger happier self (pre-marriage) and started taking Continuing Professional Ed courses, recommitted to the priority of making my body stronger/healthier to chase away fatigue and finally talk about online dating. My daughter was the one who inspired and encouraged me to start dating online and a neighbor heard about 33Kdates and said “call !!!”.   (Andrea:  What made me laugh was that Allie and her daughter (who was on Bumble) talked about dating together—and her daughter gave Allie the “push” to date herself.)

3. What was your online journey like?  Did you ever want to give up on dating or online dating?

Once I spoke with Andrea and committed to going live with online dating, it was like a whole new world unfolded and I was so curious about the experience that I dove right in! So many men with interesting profiles to meet - I filled up my calendar every week and approached each date with openness to learn about each man with a relaxed friendly vibe.


Each date was different as each man is different and I remember one that was funny to me: on one 1st date, my date knew I was interested in both science and art, and invited me to a moderated interview with 2 world-renowned physicists at a historic event space. I couldn’t wait to meet this gentleman and talk about the exchange on stage…. but he fell asleep 5 minutes in! Afterward, I didn’t mention this (to be kind) and the date ended cordially ……. Now on to the next possibility- no giving up!


4. What number date was Mark on and how did you end up choosing him as a date? Did you message him first or did he?

It was week 6 when I chose Mark on match (I reached out to him first!). I chose him because of his witty writing, importance of family/children relationships in his life and his fun relaxed natural photos (with kids too).


We had a really good phone call; he had just come back from an international trip with friends and we decided to meet. The day before our date he called to say he was sick and had gotten worse as the week progressed and was on his way to urgent care. I was hesitant to believe this but he sent a photo of himself in urgent care…. very nice. Two days later he reached out to tell me he was feeling back to himself and asked if I would still be available for our 1st date; I said yes!  


5. Did you know he was the “one” on your first date? Was there instant chemistry?


1st Date- He made reservations at a downtown very cool vibe restaurant. As I approached, I saw Mark from a distance (before he could see me) and was immediately attracted, causing me to smile at first glance, and as soon as he said hello, I knew he was like no one else. That’s chemistry.


6. What did you like about him? How did that differ from what you thought you were looking for?

1st date likes about him:

- great polished style, top to bottom

- incredibly easy to speak to in engaging and interesting conversations

- great wit, super sharp

- very attentive to me without distraction. Had me laughing and intrigued- curious to learn more

- because I decided to date a variety of men, working on my confidence with each one, I learned from each experience, I was able to define specific qualities that were a priority 


7. How did Andrea as a dating coach help you?

Andrea introduced and educated me to the possibility of finding love in the future, if I chose to search and engage. Her guidance and coaching throughout the dates were paramount. I would never have “jumped in” without her and have developed a deep trust and respect for her and her work. (BTW, she liked Mark too when we looked at him on and thought he’d be a good match for me.)


8. What advice would you give other men and women about online dating?

-Keep 1st dates light, fun, respectful & curious (even when they fall asleep)

- Be honest with your date and with yourself

- An easy smile is sexy ….

- I see dating men online as a vacation destination to visit and explore, with vast history and stories to learn. I can then decide if I want to spend more time there if I’d like.

- There are so many different personalities to meet & learn from with each interaction (call/date). Stay open to exploring one that works just for you


9. Tell us about Mark and how the relationship progressed.


Well, the relationship continues to progress exponentially:


During the 1st date we had a great connection and I was excited to learn more about Mark.


He moved business flights & meetings for the opportunity to have a 2nd date with me.

2nd date was so beautiful, with a connection that was deeper than words can explain. I knew, that night, that Mark was the one I wanted to explore solely. I expressed that I wanted to learn more about him, his kids, his grandkids, his work and where he lived.


He took my words seriously and stepped it up for 3rd date:

Mark invited me to his office, to dinner, to meet his daughter, son-in-law, and grandkids in their home, to his home, and to meet his dog…. They were all so kind. 


That’s when I knew and we both decided to become exclusive.  I’m having even more fun every time we’re together and making ongoing plans!


10. Did you share with others (friends, family) that you were trying online dating or using a dating coach? Were they positive or negative?

Yes, I did share with people close to me and happily, they were positive and thought it was about time I started dating.  I shared my experiences of online dating and being coached with everyone! My family, children, and friends are so happy for me…lots of funny stories too they (and I) enjoyed.  It was an adventure and I highly recommend it—but have a compass with a good dating coach as I did.  It helps to have a pro to bounce ideas and matches off on.

Andrea:  I attribute so much of Allie’s success to her “jumping in”, totally committed.  She was open.  Many people use the word “adventurous” to me and she personifies this quality.  She didn’t have preconceived notions of how dating should be---for example, she was always up for messaging her potential date first and men love this.  It shows confidence.


I’m happy when my clients are happy! Allie, thank you for taking the time to answer these questions.

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