The Date Doctor Has Some Funny Questions To Spice Up A First Conversation

If you’re looking for love, then listen up– Jaimy Blazynski, the Date Doctor is here!

When a lot of people start dating, whether they’re chatting on, speed dating or on a first date, they talk about the same boring topics– “What do you do for work?” “What are your hobbies?”– but Jaimy has some funny questions that will spice up any conversation.  Get the questions here…

1. If I had followed you around secretly for the past two hours, what would I have learned about you?

This conversation starter can offer insight into who this person is, and can lend itself to great stories and great topics worthy of discussing.

2.  When was the last time you laughed out loud?

If someone says a comedian or a TV show, it probably tells you they don’t have a lot of funny people they surround themselves with.

3.  What was the last white lie you told?

We all lie, constantly, but this can be another great conversation starter that can show off someone’s personality.

4.  What store do you frequent the most?

This question is fun. but it can be very telling of who a person is and what they’re into.  Gina always goes to a craft store for baking supplies, for example, and that comes up quickly and organically in conversation this way.

5.  What has been in your fridge the longest?

Spoiler alert– it’s usually salad dressing.

6.  What was your high school personality?

It’s important not to judge people by their High School personality– we all grow up and change over the years– but this question opens up to a great conversation.

7.  Who is your celebrity lookalike?

This is a cute question to ask, and it also gives an idea of what someone’s self-opinion really is.

For more advice on your love, life and relationships– or for a free tip on your dating profile– check out the Date Doctor’s website at

More from Damon Scott

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