8 Mistakes You’re Making In Your First Message To Older Women



So you’ve taken a profile photo you’re proud of, you’ve posted the perfect headline to draw in an older woman, and you’ve finally found an older woman you think you could really hit it off with. When it comes time to actually message her, you freeze. 
What should you say? You want to be intriguing, but not weird. You want to be direct, but not overbearing. You want to make her smile, but do you really actually know what an older woman finds funny? It’s good you’re taking a moment to think about this. Your first message as a younger guy trying to meet and date an older woman online is a critical task. What you say will make or break you. Here are 8 mistakes younger men trying to date older women on dating sites make when they send their first message.

Mistake #1: You don’t make the first move

This seems obvious, but so many guys fall victim to this grave mistake. If you followed our advice on making the first move in online dating,  not making the first move is like not asking for what you want- as the saying goes: if you don’t ask, the answer will always be no.

Younger guys trying to date older women on dating sites should not make the mistake of assuming older women know younger guys are interested in them.

If you don’t make the first move, that is sending the first message, you may miss out on the opportunity you’ve already put so much time and effort into. If you see an older woman you think you would hit it off with, send the first message and let her know you’re interested.

Mistake #2:   “Hey”

So many guys just like you just send this one word message to older women thinking they’ll get a response. If she’s attractive, successful, and smart- chances are she’s got a lot of young men sending her dating site messages. Sending just “hey” to an older woman you want to date is lazy, and it comes off as so. She’s far less likely to answer a young guys saying “hey” than she is one that is engaging in their first message.

Instead of just a greeting like hey, hi, hello, etc. – try adding a question that isn’t exhausting to answer, but will spark further conversation. Don’t overthink this – asking her how she’s doing this evening is twenty times more interesting and engaging than just saying hi. Try throwing out some of these important questions to ask online and see the responses you get.

Mistake #3: You try to be funny… and you aren’t funny

Plain and simple: your pick up line doesn’t do anything for you. Older women have heard it all, and they’ve never been impressed by a guy trying to get in their pants using a one-liner.

You’ve got the right idea though- you’re trying to make an older woman smile while you banter with her via a dating site. This is definitely important.

A sense of humor is one of the sexiest things a guy can have, but instead of showing her how funny you are right off, try to bring your humor in slowly and gradually throughout your conversation. Funny can be great if you can pull it off but you need to make sure your profile matches your dialogue.

Mistake #4: You come on way too strong

Telling an older woman she’s the sexiest or most beautiful woman you’ve ever seen as an opening liner is a huge mistake. Coming on too strong in the first message you send to an older woman on a dating site will make you come off as creepy, and that’s the worst thing you can possibly do. Once you’re labeled as creepy you will get blocked, ignored, or worse… screenshotted and laughed at by 9 women in a group text message.

You need to remember that with online dating there are always new women signing up, especially if you are using one of our preferred cougar dating websites. Play it cool. You definitely want her to know you’re attracted and interested in dating, but you don’t want her to think you’re desperate.

Mistake #5: You come off as only vaguely interested

This mistake is often a product of overcompensation when trying to avoid mistake #4. You’re worried about coming off as too desperate, so you play it too cool – cold even- and make it seem like you’re not really interested at all.

Older women have chased men who were uninterested and fell heartbroken in previous lives, and they’ve learned from those experiences, and will not make that mistake again. If you come off too cool, you will immediately turn older women off from you.

Avoid this mistake by slipping subtle compliments in while conversation progresses. These won’t seem desperate, but they will bring a smile to her face.

Mistake #6: You write a novel

If your opening line is more than 15 words you have written too much. This mistake creates the same product of an over-the-top compliment: you come off as desperate and needy. Older women on dating sites aren’t looking for someone who is desperate for their attention, they’re looking for someone who can cater to their wants and needs.

This is especially true if you met them at one of our recommended places to meet older women. Leave the story about how your mom and dad met for the fifth date when she asks – keep it short and sweet on the dating site.

Mistake #7: You’re dishonest

Being dishonest is one of the worst mistakes you can make on a dating site. If you lie about your age, your looks, your job, your dog, your car… it’s going to come out. When the truth comes out, you will be back at the drawing board looking for another woman. While messaging a woman on a dating site keep it real – find confidence being who you are. Older women love a confident and interested young man.

Mistake #8:  You make yourself look illiterate

Don’t mess up your chances with the woman of your dreams with a classic there, their, they’re mess up. As a younger guy, there is a certain expectation among older women that you have to be mature or intelligent for your age to be attractive. Double check the first message you send to an older woman on a dating site – it would be awful if your first impression made you look like you haven’t picked up a book since high school.

Nick Brown
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