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5 Questions to Ask Anyone You Are Dating…or NOT!

I go back and forth with shock, surprise, and awe at what singles talk about on first dates. The things I hear as a dating coach. It ranges from reticence to forwardness which can be just off-putting. There’s a balance, friends!

OK, now I want you to be you. Not a robot. Not going in with a prepared list of questions. And certainly not to be a wallflower just listening away as your date talks ad nauseam!

So, what are the things we need to figure out from what some call “the first meet” and I generally call “the first date”? Well, do I like him/her? Are they well put together? Do they match the photos you saw online? Do you like their personality? What’s the conversation like? Table manners? Manners in general?

So, here’s some questions that make sense:

1. Are you having fun with online dating?

Yes, I’d actually encourage this question. Fun and online dating---stop laughing! Because it’s a way of asking a much more important question----what we all really want to know, right? We want to know if they are a player, are they serious about a relationship, do they just want to date and a whole slew of information comes your way.

Heather, a 52-year-old female in NYC (my client) asked her date over drinks on Monday night. Wow, did she get an earful---enough to make up her mind to go on another date with him. His reply? “You know, it’s interesting---especially as an attorney I tend to meet many bankers and other attorneys professionally. I’m looking for a long-term relationship with someone outside these professions. I mean, how else would I be sitting here with you--- fashion executive—I would have never met you. So, I guess to answer your question, mostly it’s been fun”.

Wow, did Heather learn a lot from this innocuous question! Yep, he was excited to be with her.

Now, just think had she asked: What are you looking for? Ughhhh, way to put a person on the spot---plus it makes you look desperate.

And, I can’t tell you how many times a week I hear people asking this question in red----ask softly, people!


If you are not my client yet, you might like this! Did you know I offer free assessments on your online photos which are so very important? And I love helping with this! Just use this link:


2. So, what are you doing for Thanksgiving?

Of course, none of these questions I’m posing are the first things you ask. But this time of year, a great question. Why? We learn about what they celebrate, with whom, and how.

It’s fun.

I’ll give two examples from this week:

Michael, 58, (my client) from Dallas had a fun lunch date Tuesday with a very attractive, interesting woman who is a biochemist. After chatting away, he asked her what she was up to for Thanksgiving---any travel plans, etc. Her reply: “Oh, nothing. I’m a bit of a workaholic and we are working on FDA approval on a stem cell product so I generally work 70 hours a week”. The more they talked, the more she spoke of her job, her love of it, and how it consumed all her time, all the time. Definitely not what Michael was looking for. No 2nd date in the cards here.

On the other hand, last night, Jessica, 62 (my client) in Orlando called me all excited about her date with Tony. They had met for drinks---which turned into dinner. He told he hosted T-giving each year for a group of 30---both friends and family. Jessica was thrilled as they both had a Boston background in common and friends and family were a priority for both of them. Check mark for a 2nd date. (Of course, there was more she liked about him too but that clinched it for her!)

3. Why did you and your ex-break-up?

Are you cringe-ing? On a first date, it’s absolutely none of your business. Period. In fact, it’s a good way to make certain you never have second dates.

4. Any fun travel plan coming up?

Now this is fun! Who doesn’t like to talk about travel----whether it’s hiking the Camino de Santiago or a road trip to Savannah, GA by RV or to the Atlas Mountains in Morocco to a ski trip to Tahoe. You’ve just learned so much about the person---their hobbies, passions, bucket list stuff. You can see their personality come out when they are genuinely excited by something.

5. What’s your favorite holiday?

It’s that time of year for all sorts of festivities! Why this is a good question to ask? It can give you insight into your date’s religion based on the answer, which can be an important part of a relationship for some. Religion generally is a bit too much to discuss on a first date, but it can be an interesting conversation about holidays.

Happy Dating!


Andrea McGinty Founder, It’s Just Lunch (sold)

and Founder, Dating coach, Online Dating Expert, Relationship Coach


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