I Keep Going Out with Men Who Can’t Tell I’m Interested. How Can I Be a Better First Date Flirt?

In one of your videos you mentioned that while men like women who show interest on the first date, while women prefer men who leave them guessing a little bit about their interest level. I totally agree!

I grew up a very shy and insecure kid. I’m now in my 30’s, quite attractive, and overall a confident woman, but I still tend to be a little on the reserved side when meeting people in person for the first time. A few men (who I was interested in and whose company I was enjoying) have even mentioned on or after first dates that they didn’t think I was interested in them.

I smile. I ask them about themselves. I say thank you and that I had a good time at the end of the date. But a guy friend of mine pointed out that in his experience, women who don’t want to see him do these things too. He said that there is so much rejection on the guy’s end of dating and it gets really disheartening. Understandable.

Part of me thinks that if it’s really the right person with the instant chemistry I really want (yes, I know, I know, I’m aware of your teachings on instant chemistry) this won’t be an issue. Another part of me realizes there have been good men who may have shied away from asking me on another date because they didn’t think I’d say yes, and I could definitely stand to be a bit more flirtatious. But another part of me remembers reading your Why He Disappeared e-book and doesn’t want to be too eager and drive him away.

Any quick first date tips for those of us who aren’t natural flirts?

Thank you!

April

Love this question, April, because it’s thoughtful, it’s universal, and, most importantly, it’s in my wheelhouse.

Before I was an old married guy telling you kids to stop swiping and texting, I was an insatiable flirt for 35 years.

It was never a choice. It was a personality trait. My dad told me I used to flirt with waitresses when I was five. It’s innate. My mom has it. My kids have it. Most of my clients don’t. But that doesn’t mean you can’t improve considerably when you shift your mindset a little.

Being a good flirt comes from a place of irrational confidence. When you have it, you could theoretically go up to anyone on earth and assume he/she going to love you as much as you love yourself.I say he/she intentionally. Maybe I only flirted sexually with women but my flirtatious personality applied to how I spoke to old women, middle-aged men, little kids and puppies.

Flirting is enthusiastic, warm, confident, animated, and curious. It presupposes that the person in front of you likes you, is attracted to your energy, and is open to continuing the conversation. When you approach all conversations in this way, indeed, the majority of people, will, in fact, like you and want to get to know you better.

Flirtatious is confident. Needy/eager is insecure. Flirtatious assumes the answer is yes. Needy/eager assumes the answer is no.

I do an entire week on Flirting in the Meeting Men module of Love U, but that’s a decent teaser.

As for your more pointed query, let’s make a distinction between flirtatious and needy/eager which drives him away.

Flirtatious is “If you play your cards right, you may get a little action at the end of the evening.”

Needy/eager is “You’re so cute and smart and charismatic. I really hope you like me enough to see me again.”

I trust you can tell the difference.

Flirtatious is confident. Needy/eager is insecure. Flirtatious assumes the answer is yes. Needy/eager assumes the answer is no.

This is why I talk so often about being the CEO of your own love life and treating men as interns. YOU are the one who determines if you go out again and how far he gets, not him. Embrace this mentality and let men know they’re doing a good job on the date and no guy will ever have to wonder if you’re interested in him again.