Transformative First Date Topics. Conversational Adventures.

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Who’s the common denominator in each of your first dates? That’s right, it’s YOU. Let there never be again for you a lousy first date. Do your part to make sure that each of your first dates is entertaining, enriching, heart-warming, meaningful and fruitful. Make a new friend, brighten this person’s day, at the very least. In doing so, you ensure your own delightful experience as well.

My challenge to you, on each of your first dates is to go deeper in the way you find out about this other person, and the way you share yourself with this other person.

The secret to doing this well is to bring curiosity — not judgment to the questions and especially to the responses.  The only way to do this well is to NOT be attached to the response. To literally let this person be exactly who he is, who she is, without looking for the “right” answer.

This person is either “your person” for dating, love, romance, relationship, partnership … or not.

In all likelihood, your next first date will NOT be your last. Learn how to make friends along the way. Learn how to BE a friend, all along your dating journey. Whether that new “friendship” will be for 45 minutes or for 45 years.

The nature of the date has become secondary – especially since the pandemic entered the scene. What’s been developing as well is the reinvention of the first date. We have all kinds of new, creative ways for two people to meet up:  Picnic tables, park benches, Zoom calls, phone chats, text messages, Facetime, long distance exploration of all kinds. We are all learning how to share in more meaningful ways.

On your first few dates with a new prospect, ask right off, “Are you game for a Conversational Adventure?”

Some of my favorite transformational date topics are listed here:

Why are your dating? What’s  your Primary Dating Purpose?  Are you looking to meet new, interesting people? To have fun? To build your social network? Are you looking for a Keeper, trying on hats to find that perfect fit? What’s your goal when you head out to a first date?

Are you happiest when in relationship? Do you love being on your own?

What type of connection are you hoping to have?

How will you know if you have the right person?

Are you attracted to me, physically?

Given this pandemic situation, when are you comfortable touching, getting close, holding hands, kissing?

What scares you about loving again? What excites you about it? Are you afraid of giving up independence? Sharing your living space? Facing your demons? Risking loss? Do you fear hurting someone?

What are you hoping to give up when you find a partner? Vacationing alone, Cooking for One, Sleeping alone?

How many evenings a week would you like to spend with your partner? What do weekends look like, in an ideal world?

How have men (women) been disappointing you?

What’s been delightful in dating? Surprising? In what way have you enjoyed dating?

In what ways might you have disappointed someone else, in dating? Where did you miss the mark?

Human flaws. In what ways are you flawed? In what ways am I flawed?

Why are you worth the trouble? Why am I worth the trouble?

If you could relive one day in your life, which day would you choose?

A mistake I hope to never make again.

If you had to move out of state, where would you think about moving?

If you had to leave the country, where would you think about moving?

If you had the power go out in your house for 24 hours, what would you do for entertainment, that you don’t usually do?

If you’re in a grumpy mood, what’s the best thing we can do?

What’s the best way for you to make up after an argument?

The most memorable gift my mom / dad / sister / brother every gave me?

The most memorable gift I ever gave my mom / dad / sister / brother.

In an ideal relationship, how often would you have sex? What’s your favorite way to have sex? Do you have any no-go zones? What does loyalty mean to you? What does loyalty look like to you?

If we were in a relationship, who would cook? Do the dishes? Shop for groceries? Grill the meat? Clean toilets? Make breakfast? Vacuum? Dust? How many dishes should be left in the sink? Who makes coffee / tea? Who makes the Thanksgiving Turkey? Who takes the car in for service? Who handles the dry cleaning? Who pays for restaurants?  Who walks the dog? Who grooms the dog? Hotels? Airfare? Is Coach OK? If we want to bump up to Business Class / First Class, who would cover that? Fancy weekends away for our anniversary, who covers that?  Uh oh…. The hot water heater blew up – who pays for that? Kids’ college tuition – how do we save for that? Mom broke her hip, can she stay with us for a month?

What if we were to vote differently?

What if one of us wanted to go to church on Sundays, and the other didn’t? What if one of us wants to observe Shabbat on Fridays, and the other doesn’t really care much about that?

What if one of us wants to eat veggies only and the other is a carnivore?

What will cause you to put your foot down?

How would you LOVE to celebrate your Bday? Valentine’s day? A wide-open Sunday?

How do you like to get gifts? Poem? Card? Surprises? How do you like to see love expressed?

If you received $1,000,000 and you had to give half of it away to charity, where would you place the money?


You can see… this list can go on and on.

My challenge to you – dare to create your own list and USE IT on your early dates. Before the clothes start flying. I predict it’ll change everything for you.

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