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8 Things You Should Never Mention In A Message To A Woman Online

Things you should never mention in a message if you want to land a date

We live in a digital age. You order meals, book vacations, and keep in touch with friends and family online. You even fall in love online. The internet has changed the way we do things, making it easier to get exactly what we want. With over 7,500 dating sites, there’s a love connection for every type. But getting there is only half the battle. You still have to create an appealing profile, find a woman you like, and send a message that gets her attention.

Things You Should Never Mention in a Message

Setting up your profile is fairly straightforward. Narrowing down the woman you want to meet is easy enough. Sending your first message that elicits a response is trickier. Older women are overwhelmed with incoming messages unless you are on the best sites. Using the best platforms will definitely improve your message response rate.

We suggest trying one of the proven sites from our yearly review of tested and true cougar dating websites. Her other admirers might know what to include in their message, but they don’t know what to keep out. This is where you have the advantage.

Here are 8 things you should never mention in a message to an older woman online.


Even if you mean well, mentioning an older woman’s age can come across as insulting. This isn't how you should talk to girls online. You might tell her she’s beautiful for her age. In your mind, you’re complimenting her beauty. But she may interpret that as you telling her she looks good for an old hag. Older women can be sensitive about their age, no matter how beautiful they are.

There’s still some lingering stigma around relationships between older women and younger guys. Mentioning her age can provoke anxiety about these stigmas. It’s best to play it safe and avoid the topic. Besides, her age isn’t the most interesting thing about her, so it shouldn’t be the subject of your message.

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Limitations or disabilities

As you date older and older women it becomes increasingly likely that they're dealing with some kind of limitation or disability in their life. While certainly a challenge for them it doesn't mean that they won't be fantastic partners or companions. In fact, there is even an entire dating site dedicated to helping people like this find dating success called Soulful Encounters.

When you're messaging women, it's a smart idea to avoid making any initial comment on a perceived disability or limitation she might have. If you're right she may be sensitive about it and if you're wrong you'll look very foolish. Either way, you can't win so avoid it completely at the beginning.


Insecurities about being younger can manifest in several ways. Don’t put her on a pedestal because of her experience. Be yourself and avoid trying to act older than you are. She’ll see through it and become uninterested. Don’t peacock by bragging about the things you own or the people you know — older women don’t care for those kinds of things.

If she responds to your message with questions, answer them. Don’t deflect or beat around the bush. Older women value a guy who is straightforward and transparent. If she doesn’t answer immediately, be patient. Women get an average of three messages a day and take longer to respond.

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Lack of Experience

Having a lack of experience doesn’t automatically exclude you from the pool. Some older women dig guys with less experience. They appreciate the adaptability of a guy who isn’t set in his ways. It gives them a chance to teach their guy what they like. There’s opportunity for compromise and synergy.

But that doesn’t mean you want to advertise your lack of experience. It’s not the best way to introduce yourself to an older woman. Give her the impression you can be a great partner. Focus on the things you’re good at rather than the things you’re less familiar with.

Your Differences

Before you send your first message to an older woman, make sure she’s a good match. Most dating sites allow you to narrow your search by location, age, keywords, and other criteria. Studies show you’ll be more attracted to women who live close to you, so that should help you narrow it down. Science also shows you’ll be happier with a woman who has more in common with you. Leverage that by focusing on the things you have in common when you write your message.

Instead of arguing why she’s wrong “Harry Potter” is the worst series ever written, give her all the reasons you’re perfect for each other. You can talk about “Harry Potter” later after you’ve primed her with sweet talk and a few glasses of Chardonnay.

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Things You Should Never Mention In A Message? Commitment

Older women are no strangers to commitment. In fact, they usually appreciate a guy who values loyalty. But your message isn’t the place to propose eternal devotion. It’s the place to introduce yourself. Maybe ask her a few questions online. If she looks like she's into you you can also flirt with her. The point is to be playful, in an endearing way. Many older women are just returning to the dating pool after a long-term relationship and the last thing they want is an immediate proposition of allegiance.

“Off-Limit” Topics

Some topics aren’t appropriate for online messages. Some subjects are a better fit for third-date conversations when you can discuss them in person. An online message doesn’t lend itself to nuanced dialogue. Misunderstandings can happen and feelings can get hurt. It’s too easy to simply not respond, rather than taking a moment to right the error.

Typical off-limit topics include politics, religion, health issues, recreational drug habits, and finances. As tempting as it might be to tell her about your case of Basorexia, hold off for now. If she opens a dialogue about an off-limit topic, use it as an opportunity. Tell her you’d love to talk about the World Nuclear Association, over a delicious meal.

Other Women

There’s an unspoken understanding that you’re messaging other women (even if you’re not). Just as there’s an understanding the woman you’re messaging may be having conversations with other suitors. That’s part of what makes online dating exciting. She chooses you; not because you’re the only option, but because you’re the best option. So there’s no need to remind her of all the other women you’re pursuing.

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Pick-Up Lines

Most older women have been dating long enough to know when they’re being adulated. They generally don’t respond to cheesy pick-up lines. They want a guy who is genuine and mature. Their days of playing games are behind them and they usually don’t want to hit the repeat button. For most older women, a guy messaging her a pick-up line screams “player.” Older women are particularly keen on avoiding guys like this.

In place of pick-up lines, try a sincere compliment. Did you see something on her profile that struck your interest? Let her know. Aim for a compliment that isn’t about her physical features. Try complimenting her on a characteristic she had to earn. Her intelligence, her career, achieving a goal. Compliments like that will make you stand out from the crowd.

You’re on the right track by giving online dating a chance. Science shows that people who met their spouse online are happier and less likely to divorce. Even if you don’t find your soulmate, it’s a cost-effective dating method. According to one study, you can save about $6400 versus traditional dating methods.

There are some great online dating sites for finding older women. Give them a try and flex your message muscles. Who knows, you might just meet the love of your life.


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