7 Tips for Dating a Shy MILF

Guess what? Not all MILFs are the confidence monsters we imagine them to be.

Alright, plenty are; but not in today’s article. This one is dedicated to the MILFs who, despite their age and experience, still rest on the shy side of life.

If you’re about to date a shy MILF, you may wanna keep the big-guns holstered and start with some less intimidating fare for a first date. 

Read: MILF Dating Sites That Work

Shy MILF Dating tips

Here are seven tips and ideas for your first date with a shy MILF.

1. Don’t take her anywhere that might make her feel old.

I know you’re just dying to introduce her to this year’s Comicon lineup, but save that outing for you and your superhero-loving pals.

And speaking of your pals: a shy MILF probably won’t want to go to your friend’s “My Parents Are Out Of Town” party. In fact—

2. Don’t introduce her to your friends until she’s comfortable with you.

If she’s shy, she’ll be anxiety-ridden at the thought of being scrutinized by an army of raving young uns.

3. Don’t suggest watching porn together.

Many couples do it, but shy people peek at porn and can feel self-conscious watching it even while alone. It can make them feel weird. The thought of experiencing it with someone else might give her a stroke.

Shy MILF on a date.
Take it slow with a shy MILF.

4. Take her to a noisy restaurant rather than a candlelit one.

Quiet restaurants can draw attention —and quite possibly judgement — from other patrons who are all too eager to whisper about the age difference. She’ll go quiet.

5. Take her for a walk.

Nothing would placate her more. It’s private, romantic, and allows her the opportunity to talk and listen without fear of being watched.

6. Don’t ask her for a full history on the first date.

Take for granted that your shy MILF is enough to have way more baggage than you. Much has passed in her life, possibly not all good, and she’ll hardly be in a rush to spill the beans so early. She’ll worry you’ll judge her.

Go slowly. Be patient. If you really like her, a shy MILF will be worth the wait.

And remember: inside every shy person is a sex machine just waiting to burst forth!

Read: Where to Meet Horny MILFs

Have you dated a shy cougar or MILF? Tell us about your experience.

Tell us what you think

Notify of
Inline Feedbacks
View all comments