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Fifteen minutes into meeting him, you realize that sexy skirt you just picked up at your favorite boutique to boost your first-date confidence was worth every penny.

You look sassy as it hikes up just a bit when you lean back in your chair. Trying hard not to stare into his deep blue eyes, you sip your Viognier and you hang on his every word. Girlfriend, just so you know, he may hang on every one of yours too and when he does, he may be making inaccurate judgments about who you are that could culminate in a “Good night, it was nice to meet you” and nothing more.

Keeper? Are You One of Them?Can I tell you what he’s watching for?

A man who hopes to date you will want to provide for you.

Just go with me on this one. I’m not saying he’s paying next month’s rent or running out to buy you that electric fondue maker you’ve been eyeing, but he will want to contribute to your life if you end up being his girl. He’ll be looking to see if he can afford you. He won’t ask what you need, he’ll listen, and based on these four things he’ll sort you potentially in or out:

  • He will account for what he believes all women need.
  • He figures you need the things you already have.
  • He assesses the lifestyle you’ve had in the past. For instance, he’ll consider what you had in a previous marriage, or growing up.
  • He’ll determine what you need based on what you talk about.

So when you’re sliding your smartphone his way for him to view the photo of the new Tesla, he just might say, “That’s a beautiful car and it suits you” while thinking, “Too bad I can’t afford her, I liked this one.” Done.

Now, if you need him to buy you that Tesla, you’ve just done an effective job of sorting him out. But if you were simply showing him that car because you think it’s cute, you’ve just sent him the wrong message.

To help avoid inaccurate evaluations, start by noticing what you bring to a first date as your conversation starters.

What you talk about on a first date might be considered your top priorities — I mean, you’re leading with them, after all. Instead of Tesla photos, roll out your unique self by sharing what you’re passionate about:

  • Who’s your underdog?
  • What’s your favorite TED talk, and why?

If your hobby is freeform sketching, what inspires you? Who do you get to be when you’re in the zone? When you talk about your passions, there’s azinginess in your energy and sparkle in your eyes, it’s deliciously enchanting.

Talk about the things that make you happy, or share what you love about your life.

What did you always want to be when you were a kid, and how did that dream get derailed?

Did you notice that money, physical items, and status don’t naturally surface in those topics? That’s on purpose. Am I telling you to downplay your lifestyle? Nope. Just be aware that when you share your love for Rome and how you plan to spend three weeks, there he might think, “Gee, can I pay for both of us to go to Rome for three weeks every year? What about where I want to go? Can I take all that time off of work? Is my passport up to date?”

If Rome is always a first date topic because it’s a priority in your life then consider giving him the facts he needs, because it won’t occur to him to ask you for them. You could say, “I go to Rome every spring, I love Rome. I always spend three weeks there. Over the years I’ve treated friends, or we’ve gone Dutch, sometimes they meet me there for a few days, and some years I’ve gone solo. I’m happy there when I share it and when I have it all to myself.” Quality information like that helps lead to another date, and who knows, maybe even a romantic, Italian adventure together.

Wendy Newman

Wendy Newman is a dating, sex and relationship expert and has led hundreds of workshops to thousands of people internationally on the topics of understanding men, sex, dating, and partnership of all kinds.

Over the past decade, she’s interviewed thousands of men on sex, dating, relationships and women.  She’s conducted polls, had intimate one-on-one discussions, and has witnessed well over one hundred panels of men talking on these topics.

Wendy was a compassionate fellow dater who navigated her way through 120 first dates before she retired my favorite dating scarf for first date #121.  They live happily ever after in San Francisco, California.

Her book 121 First Dates: How to Succeed at Online Dating, Fall in Love & Live Happily Ever After (Really!) offers practical wisdom and guidance for smart, successful single woman.  Readers will gain tools, hope and be entertained by her tell-all stories of actual first dates.  The book is published by Simon & Schuster will be out in stores in January, and available for pre-order on Amazon here

What Do You Think?

4 Comments | Join the discussion

  • JaiDei Aug 5, 2015 at 8:18 am

    Great article Wendy! It’s a good reminder for me to remember to share my heart’s desire, my passion, what makes me happy. One of my favorite date question is what is one of your happier childhood memories. This question allows me to live vicariously through his experience & it takes the awkwardness out of the date.

    • Wendy Newman   JaiDei Aug 6, 2015 at 9:22 am

      Good question, JaiDei!

      I also like “What do you love about your life?” because it makes people happy to talk about what they love and what works.


  • Anon Aug 1, 2015 at 7:01 am

    As a guy, this article is … Just so far off. You are correct in that guys are summing up a girl on being high maintence or not… But not at all in the way you described

    • Wendy Newman   Anon Aug 3, 2015 at 7:56 pm

      Thanks for your perspective, Anon.


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