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

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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.

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.

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.