How To Ask A Senior Woman Out

Senior Dating

How to Ask a Senior Woman Out

Kara Pound

Written by: Kara Pound

Kara Pound

Kara Pound is an award-winning journalist based in St. Augustine, Florida. She holds a bachelor's degree in journalism from Flagler College. Her work has been published in INKED, Natural Awakenings, Design Aglow, Memphis Flyer, Jacksonville Magazine, E/Environmental Magazine, and dozens more. Check out some of Kara's work at

Edited by: Lillian Castro

Lillian Castro

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Asking a woman out who is in her 50s, 60s, 70s or beyond is definitely more difficult than asking out a 20- or 30-something woman.

When you’re young, you’re not quite sure what kind of woman you want to spend your life with. That’s why you date around — to figure it out. When you’re older, you’re more wise and confident of the type of life partner you’re looking for.

Gentlemen, it’s no secret that asking a senior woman out on a date is more nerve-racking. But that doesn’t mean it’s impossible.

The following are tips for senior men to ask out senior women, including how you should do it and what you should take into account.

1. She sees through all the BS.

Don’t try and pull one over on a woman who has lived life. She has experience and wisdom and will see right through your games and/or lies. If you are honest with her and confident, then you will have a much better shot.

2. Don’t waste her time.

If you’re not serious about dating and are really just looking for a fling, be upfront and tell her.

Say, “Honestly, I’ve done the whole marriage thing and I’m really just looking for a fun woman to travel with and go out to dinner.” This way you both know where you stand.

If you think she’s interested in seeing you another time, recommend another place to meet for a first date.

3. Don’t beat around the bush.

If you want to ask her out, then ask her out. Don’t stalk her, don’t make her feel uncomfortable and definitely don’t beat around the bush.

Women who have lived just want to continue living. They don’t need everything analyzed beyond recognition.

4. Treat her with kindness and sincerity.

At her age, she’s seen it all — the men who lie, the men who cheat, the men who can’t commit. If you want a senior woman to take you seriously, then treat her with the utmost kindness, sincerity and respect.

It’s true that a senior woman is a tougher nut to crack than her younger counterparts, but that doesn’t mean it’s impossible. She may be just as hesitant as you are when you first interact. Choose your words wisely and compliment her without disrespecting her.

If you understand that she’s a mature, wise woman with a no-nonsense personality, you’ll be as good as gold.

5. Keep calm and trust your instincts.

Gentleman, this isn’t your first rodeo. Remember you’re not impressing a mysterious college classmate, instead, you are working with a calm and experienced woman with a lot of love to keep giving.

As long as you approach her with the collective composure you’ve accumulated over your years, you’ll be sure to spark some interest with your new crush.


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