Flirting for Introverts: The “Flirt a Day Challenge”

Posted by in dating after divorce, dating in midlife, flirting | 4 comments

Flirting for Introverts

I often write about the importance of getting out of your house and meeting potential dates out in the real world. I encourage you to make eye contact, smile, and say “hi” to men every day. This seemingly simple act is not as easy as it seems, especially for the introverts among us.

According to Susan Cain, author of Quiet: The Power of Introverts in a World that Can’t Stop Talking, one out of every two or three people you know is an introvert. That includes me. I was always the introspective one, the one who shied away from the limelight, the one who whispered the funny lines under my breath while my loud-mouthed extroverted friends would repeat them and get all the credit. After my divorce, I decided that I’d played small long enough. I vowed to push out of my comfort zone on a regular basis. And flirting for introverts is way out of our comfort zone!

4 Steps to Make Flirting for Introverts Easier

1. Take small steps. You might be thinking, “I’m out here flirting at Starbucks with a total stranger because I am hoping one of these latté drinkers will be my future husband.” Too future- oriented and not so realistic! Instead, think small. “I’m out here flirting because I’m taking one small step in lightening up and being playful. This will help me have more success in my love life.”

2. Reframe the flirt. See #1. What is flirting to you? Make a list of adjectives you associate with flirting. Is that list filled with negative connotations? If so, rewrite your list and fill it with words that describe your new positive perspective on flirting. If you’re not yet feeling it, write words that describe how you’d LIKE to view flirting. Instead of thinking of flirting as an overtly sexual come-on like I used to, think of it as something else; a door opening, a conversation starting, a playful interaction, a great way to practice being bolder and more confident in social situations.

3. Just do it! Stop over-thinking and start doing. The act of flirting on a regular basis will make you more comfortable with flirting. Don’t just flirt with potential partners. Flirt with everyone – the cashier at the grocery store (call him or her by name – it’s pinned onto their shirt), men and women, babies and young children. The more comfortable you are getting out of your head and lightening up, the easier it will be to flirt with your potential Mr. Right.

4. Get support. That’s where this challenge comes in. A client suggested that since it’s uncomfortable for her to flirt, wouldn’t it be more fun if we made it a group challenge? I loved the idea. I’m hoping that lots of you will love it, too.

The rules for the “Flirt a Day Challenge”

1. Sign up at the bottom of the blog in the comment section. Make a commitment to a flirt a day. Saying it out loud makes it more accountable. I’m supporting your efforts. You don’t have to be a good flirt. This is a fun experiment to help make flirting more organic for you.

2. Make a list of where single men your age might hang out. The grocery store at 7 or 8 PM when men shop after work (check their shopping carts for bachelor food – a few potatoes, a steak, a six-pack of beer), the post office at midday, the library on a Saturday or Sunday, the dog park, a hiking Meetup ( Every time you think of a new place, write it down.

3. Make a commitment to visit one new place a week. Just do it. I know it’s scary. Ask the guy at the grocery store how he cooks his steak. Ask the man next to you at Starbucks if he can help you decide on the lemon poppy muffin vs. the cranberry orange scone. Men love to problem solve, so this is a great way to engage him.

4.  Make eye contact, smile and say hi to a new man every day. It’s simple. Each time you do it, it will get easier. Really.

5. Share what happens in the comment section. We want to know how you’re doing. Is it hard for you to flirt? Did a cute guy return your smile, start a conversation, ask you out?

Who’s in for the Flirt a Day Challenge? Any questions? What are you waiting for? Let’s get the Flirting for Introverts Revolution started!

“Feel the fear and flirt anyway.”

– Sandy Weiner

Can’t wait to see your comments below. Are you in?

P.S. If you’re too shy to post in the comments section, I understand. Join my private Facebook group and post there! Happy flirting 🙂



  1. I’m loving this. I will flirt once a day until I get comfortable.

  2. Marilynn,

    So glad you’ll join us in the Flirt a Day Challenge. Please post updates on how it feels to flirt. I’d love to hear how it goes for you.

  3. I’m an introvert, so this is perfect for me. I’ll start at the hardware store tomorrow.

  4. Courage and conviction—a winning combination! Let me know how it goes 🙂

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