9 Proven Tips To Improve Your First Message Response Rate With Older Women

Tip to improve your first message response rate

Looking to get past that crucial first obstacle where online dating is concerned: the first message? In this article, we take a look at 9 proven tips that will improve your first message response rate with older women.

The thing you’ve gotta remember about older women is that they’ve got more dating experience than women your own age. They tend to know exactly what they want. If you thought younger women were selective, be prepared for some major selectivity issues from older women. I’m talking “won’t even reply to George Clooney if there’s a typo in his profile” selective.

The key to any opening message is knowing what a woman wants. You’re going to totally strike out if you don’t get this. If you’ve got literally no idea what she wants to see in her inbox, your opening message rate is going to read:

Sent: 100 messages

Read: 100 messages

Responded: 1*

Blocked: 2 (after the first 80 knock-backs, you’ll start getting weird and desperate, at which point the blocks will come thick and fast!)

*The only woman who responded was Judy, 68, widowed, wants a dance partner – and who you messaged just to see if this damn app was working.

I’m a big fan of metrics. When it comes to my opening message? I’m prepared to keep tweaking it until I see the results. And what I’ve come to learn is that it isn’t just your opening message that matters, it’s the whole package – from your profile to your pic and all that’s in between. You want her (not Judy) to reply so you can be the cat that got the cream? You’ve gotta think outside the box.

Improving Your First Message Response Rate

Here are 9 proven tips that will improve your first message response rate with older women. While these tips will help you out, you still have to be using the highest quality dating sites for meeting attractive single women to maximize their effectiveness.

Upload Your Most Mature-Looking Pic(s)

Sure, she’s looking for a younger man. But how young do you think she’s talking? If your profile pic looks too young, you run the risk of making her think you’re a baby . . . and she isn’t looking for that.

You need to choose one of your most mature-looking pictures for your profile pic. Make sure you look older than a late-teen, avoid anything video game related, and send out the impression that you’re wise and mature for your age. It’s all about targeting the right people with the right image and looking unwashed with light beer cans all over the place in the background isn’t going to cut it.

Emphasise Your Career In Your Profile

Older women generally won’t date a guy who makes less money than them. I learned this the hard way when, as a hard-up student, I tried to woo a woman with fries after a movie.

She never returned my calls.

If you’ve got a solid career and are doing well? Emphasise it in your profile. It’s like catnip to the ladies. It’s your leverage — use it.

Compliment Her

I’ve heard it said that girls don’t appreciate being complimented by a guy in the first message. When it comes to older women? It’s totally different!

Think about it — You’re a younger, good-looking guy messaging a woman who’s older than you. If you can flatter her with a compliment, you could end up making her day. And she’ll be really receptive to that.

Mention Her Age

There are do’s and don’ts when it comes to mentioning a woman’s age in your first message.

Don’t say: “You’re hot for your age!”

Do say: “I can’t believe a woman your age is single.”

It’s charming, inoffensive, and should flatter her.

Mentioning her age is a dicey one, however, so you could shoot a few messages to different women to see what works and what doesn’t for you specifically.

Don’t Be A Douche

Ever heard women your age say “I am SO done with being treated like rubbish?” It’s because some guys are assholes! Thing is, those same women keep on going back to the bad boys.

I know, annoying. But it’s a maturity thing and there comes a time when women really are finished with jerks.

For older women, that time is now. Clean up your profile so that you don’t come across as a preening, posturing douche who thinks he’s God’s gift to women. Ditch the pic of your car. It might impress starry-eyed young women, but older women tend not to like guys who are full of themselves.

On that note . . .

Don’t Pout Or Pose

I was messaging a woman once who said something really instructive to me:

“I usually don’t reply to guys who pose and pout in their photos. They tend to be full of themselves, and that’s a major turn-off.”

In other words, drop the act in your pictures. Stop trying too hard to be cool and hot — just be yourself. Hot often doesn’t cut it with older women. They want realness and a down-to-earth guy who’s honest. They’re looking for maturity and fish-lipping a camera comes off as childish.

As you scan your pics for ones to upload, you can choose one or two hot ones, of course. But prioritize realness first. What you think is hot, she might think is just ridiculous.

Be Funny

Make her laugh with your opening salvo, but also make her laugh with your profile.

Younger women don’t always view your profile before replying, tending to be more offensive. Older women, though, will be more inclined to properly check you out before they reply. So it’s a good idea to be funny with your opening message, but also on your profile.

You don’t need to go overboard and be the class clown, but it’d be nice if you could show her that you’ve got a good sense of humor.

Be A Gentleman

This shouldn’t come as a surprise, but be a gentleman too.

Be good with words. As much as possible, try to come across as though you’d be well spoken and well-educated in real life. An older woman is on the lookout for a real man, not a boy. So be polite in your first message, charm her with your wit and send out the impression that you’re a gentleman.

Make An Early Connection

Most women like it when a guy puts in a bit of effort with his first message. But older women really appreciate it.

To grab her attention as soon as possible, you need to make an early connection. You can do this by talking about something that’s close to her heart. Whatever she lists as her interests are not simply there to fill up the space – these are things she cares about. If she’s listed politics as her interest? Establish a connection by making a passing comment about the political climate.

Don’t worry about getting serious in your opening message. The chances are, she’ll appreciate it. Good conversation matters and finding some common ground to talk will open up the doors to further conversation.


Getting the attention of an older woman is all about knowing what she wants to see. Be charming. Be funny. Be real. Be a gentleman. Don’t preen. Don’t pose. Don’t show her your car.

Not unless you wanna end up with Judy.

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