Speed Dating Newbie Nancy - Just Jill

Speed Dating Donna - Just Jill

Just Jill is the creation of Jill Cohen Morris. Jill is an avid rambler and married mother of two from Toronto, Canada with a remarkable zest for life and a fabulous sense of humor. 

Dear Just Jill

I am in my mid 50s, divorced and new to the dating world. I signed myself up for a speed dating event.  I somewhat regret it… actually I’m terrified, excited and even proud of myself.

I have seven minutes with each potential suitor. Are they even called suitors anymore lol!!

My question is what would you ask to determine a potential partner’s character, morals and values when you only have seven minutes. Or do you focus on the basics … career, family, hobbies? Likes or dislikes?

Have any Sole Sisters participated in something like this?

What’s a gal to do?

Sincerely,

Speed Dating Donna

Sole Sister Advice & Comments 

  • I recently participated in a unique conversation starter. The question was, "What is something you don't want me to know about you? " The conversations that followed were deep, insightful, honest, and raw, cutting to the chase.

  • Definitely avoid anything that feels like a resume/CV, as nothing exciting ever comes from that. Think creatively about a maximum of three things that would delight you in a partner and focus on how to figure those out in a fun way. More broadly, think of speed dating as a lark. Be fun, be curious, and don’t take it too seriously!

  • It does sound terrifying and exciting all at the same time. I think mainly, because it’s your first time, you go in with zero expectations. Treat it like the first pancake; it’s a throwaway where you learn for the next time. When I meet new people I tend to steer away from "what do you do for a living",  and focus on what they like to do in their spare time. Really, you only have 3 ½ minutes each to talk about yourselves.

  • Think about what the object of the event is. It’s not a job interview. It’s a moment to meet someone to see if you find them interesting or attractive enough to go on a real date. It is more about connecting than digging for information. So, instead of thinking of questions, try to tune in, relax, and engage with that person in the moment. Future connections tend to be led with feeling and mutual attunement. Do they make you laugh? Do they make you think? Not the often performative questions we ask or answer in  “interviews". Just be yourself, slow down your vibe, and make contact.

  • I previously attended a speed dating event. We were given a list of questions that you could use. I hated the event.
  • How many countries have you traveled to? That would be one of my questions.

  • Hello! I coach people through the dating process as a mindset/energy coach! I help loads of people in my online sessions. I am 55 and have been through the whole experience of single, middle-aged dating and have some great guidance. Here’s some for free! Firstly, you need to get into a positive mindset before you step foot near the event! Secondly - it’s all about energy and trusting your intuitive guidance. Thirdly - you attract what you are. So it’s best to know clearly where you are at and what you want from this next stage of your life and from a partner. It can be a rich and wonderful experience if you go in with a growth mindset and positive energy. Good luck. So excited for you!! Remember…everything is happening for your greater good, no matter what the outcome. It’s all about getting back to your own heart. That’s the journey.

  • When I was online dating, I would ask, “What is your favorite ice cream?”. It was a way to see if they were fun-loving, as it was not really about the ice cream but more about how they react to the question

  • I would ask what they do when they have nothing scheduled for a day

  • I suggest seeing how he talks about his mother and kids. I think this speaks huge to character

  • "What are you looking forward to?" Is most often my get-to- know-you question. It works a charm because it is not about what was but about what might be.

  • If you knew we were going into lockdown again (re COVID), what would you do? Who would you want as your inner circle for the next 6 months... Etc. What's your favorite way to spend a Sunday afternoon? What do you have for supper at least once a week? If you won $10,000 this afternoon, what would you do with it?

  • I remember speed dating years ago..my friend met her now husband at one! I didn’t think they still existed, but I think they’re a great idea but nerve-wracking too! I must look into this more

  • I admit it’s been a long while since I dated, but something I always tell people is to look at how the other person handles conflict. We are all the nicest people in the world when we get our way. The real question is how do we all handle not getting our way. Obviously, this might not be a question for a seven-minute conversation, but it is one that is important to have early on. Consider spending your 3 minutes looking for things in common. It’s all fine and good if they are good people who value family and relationships, but if you don’t have any hobbies or activities in common, it likely won’t matter. You can find out about other important things at the next stage. Good luck. You should be proud of yourself for putting yourself out there!!!

  • What he learned from previous relationships, deal breakers, what he enjoys doing the most, and activities he doesn't like. Also, gauge his interest in you by how well he listens.

  • Hmmm, I met hubby 28 yrs ago through a matchmaking service. It worked great! It cost money for the service so you had committed people. ($2500 for men, $1600 for women) Today's free apps and speed dating events are too easy and cheap. I've been told by a number of people that many men now don't want commitment anymore. They quite like the smorgasbord of choices. They can have a new flavor each month! It's disgusting, but it's true. For speed dating, I suppose it's attitude. If one goes in looking for a long-term relationship, there will probably be disappointment. But going in looking for someone to do fun activities with can lead to that first date. The more you do activities, the easier it becomes to see if you're compatible in the ways that are important to you. And if it's not a long-term relationship, maybe you get a fun companion out of it. Who knows where these adventures turn out when we're curious and open? It's kind of like relationship rambling! You start out, and you never know what you're going to discover!

  • I have two favorite questions: Do you have a valid passport, and what’s your fatal flaw?

  • Listen to your intuition. Ask them about their passions and interests and if they have children. I think it's important to see how they talk about their kids because it's a signal for healthy relationships. Be optimistic and open. Just look at it as fun and relaxing. Don't have any high expectations. But most importantly, trust your gut.

  • Ask them what they like to do outside of work. Where would they go on a first date? The best gift they've ever received. The best, most thoughtful gift they've ever given. What would they like to do that they haven't yet tried? Favorite music genre, favorite food....speed dating is a numbers game...if your person is there, you could make a connection; if not, at least you get the experience...they'll probably give you some sample questions. 

SSR doesn't endorse the advice or content shared in this column. Our goal is to access the wisdom of our incredible Sole Sisters.

 READ MORE > Ask Just Jill, Rambler Cafe Blog


1 comment


  • Karen Biggs

    Thanks for this article Jill. My estrogen blocking pills for my breast cancer are affecting my muscles and joints. It is hard not to compare with those around me!


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