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First Date Success: 14 Tips to Have Him Asking To See You Again



On paper you’re impressive: educated, accomplished, independent, attractive and have a great job. So, why didn’t he call you back after the first date?

“I thought the date went well. I don’t understand why he didn’t call again.”


I hear this often from clients who, like a hamster on a wheel, keep going on first dates and fewer second and third dates.

With the prevalence of online dating, expecting perfection causes more failed first dates than ever before. It only takes a click of a button or swipe to meet someone perceived to be ‘better.’

More than this, I was curious as to what keeps a man from asking a woman out for a second and third date. I investigated by listening to panels of men being interviewed on the topic and asking them myself. My query of men included friends, acquaintances and a sampling of men I encountered in the course of my day over several weeks.

What I discovered:

The Boss Lady, as Rachel Greenwald, author of “Why He Didn’t Call You Back: 1,000 Guys Reveal What They REALLY Thought About You After Your Date” refers to her, is alive and well among us very competent and successful women.


She is a stereotype, and the man walks away from the date thinking that he’s more interested in hiring her than dating her. He perceives her to be argumentative, competitive, not feminine, controlling and not nurturing.

Despite this, your date is making assumptions about you based on intimations you’re making without your awareness. A woman does the same with the man. With recognition of how you’re coming across, tweaking the way in which you’re presenting yourself can inspire him to ask for a second and third date.


Don’t change who you are, rather I encourage you to modify what you’re putting out on this all-important first date.

Here are 14 tips to landing that second and third date:

  1. Don’t come straight from work in your business suit. Paging The Boss Lady.

  2. Don’t lead with your stuff – listing your accomplishments, all the trips you’ve taken, your house, talking ad nauseam about your job as opposed to mentioning your work, if asked, is your stuff.

  3. Don’t share your life story and all your requirements that you’re seeking in a relationship partner. When you do this – you’ve given him all the information he needs, so, why would he ask you out again?

  4. Don’t refer to your former boyfriend or ex-husband by name or share your health history. There is such a thing as too much information.

  5. Do be on time. It shows you respect his time. Plan for extra drive time if you’re getting somewhere during rush hour traffic.

  6. Do let him plan and pay for the date. It creates the space for the masculine energy to show up.

  7. Do have a life that you love. Share your passions; what makes you happy. Perhaps it’s painting, golf or writing, as examples.

  8. Do allow the mystery to unfold. Be the present that you are and let someone slowly unwrap that to the gift inside.

  9. Do reveal something about yourself (non medical, of course). When you do this, he thinks, “Wow, she trusts me. I’d like to know more.”

  10. Do be curious. Ask him about his passions and pastimes. It shows you’re interested.

  11. Do put your phone away – It seems obvious, but, this social blunder is a top offender. Put your phone on silent and in your purse – not on the table. Giving him your undivided attention makes him feel important.

  12. Do have fun, laugh and smile. It shows the playful side of you.

  13. Do compliment him on his restaurant choice. He wants to know that he pleased you.

  14. Do express appreciation for him making the plans and treating you to dinner. Every man craves recognition for the effort he’s made.

A man follows up because of how the woman makes him feel. While not fair, instant judgments are being made. Information is being extracted from your gestures and comments.


When you turn up the softer side of you for your date, it’s your femininity and all that entails that stirs him to pursue you for a second date.

Ever wondered why he didn't call back? What happened?


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