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Online Dating: 8 Proven Tips To Help Improve Your First Message Response Rate With Cougars

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Many guys who use online dating find messaging older women a daunting prospect. While it’s hard enough to put a message together for someone your own age, it’s extra hard when she’s a few years older. Maybe it’s all her life experience, the feeling that she’s seen it all before or worrying about looking immature.

Whatever it is, it adds pressure and results in even fewer responses. This means you can spend all day sending out messages only to get zero replies. So, what should you say to impress her and get her to write back?

How to get a response to your first message to an older woman


First, you have to make sure you’re on the right website. The more users and the highest percentage of actual responses put a website above others. As you will find in the end-to-end Cougar Life review here, there really isn’t another site that matches them.

Trial and error is not the way to go when messaging older women. Simply put, you only get one chance. If she doesn’t like your first message enough to reply, she’s not going to open the second email.

But while there’s no magic formula that works every time, there are certain points you should be checking off in all your messages. Let’s get started.

1) No one-word messages

You may think you’re being cute, giving her a ‘wink’ or a ‘nudge’ to get her to check out your profile, but unless she’s desperate or a bot, “Hi” never works. She gets 50 of these one-word messages daily and yours isn’t any different.

Imagine your first message is a flyer for a new business opening. It needs information, it must be attractive and it should prompt her to want to know more. You can do this with a couple of emojis either.

It doesn’t need to be three pages long – and it shouldn’t be – but it needs to give her something to go on. After reading it, she should want to check out your profile.

To do this, you’ll need to start by introducing yourself first. Say who you are, what you’re into and what you’re looking for. Hopefully, this introduction will encourage her to keep reading and increase your chances of a reply.

2) Give a genuine compliment

After the introduction, a well-structured and thoughtful compliment is the best approach. If you’re afraid to give compliments because they usually elicit eye rolls from your recipient, you’re doing them wrong. Generic throw-outs like, attractive, hot and sexy are not compliments, they’re just single words. Compliments are specific – they apply to the individual. So in order to give her one, you’ll need to look at her photo and profile and decide what you like about her.

Does she have nice eyes, a great smile or a cute nose? Great, then tell her. Some compliments work better than others. Hair and clothing remarks are less effective as they’re not really part of her.

However, if you can give her an achievement or personality-based compliment, you’ll find that goes much further. If you’re impressed she got her masters in psychology, tell her. If you’re touched by her work with Habitat for Humanity, let her know. These thoughtful compliments are gold dust.

3) Talk romance

In their quest to sound mature and sensible, many younger guys take the hard-line approach when messaging older women and forget to flirt. You don’t need to come off as Pepe Le Pew, but you do need to get the tone right. This is a romantic message, not a business inquiry.

If you’re worried about being too romantic too soon, before you’ve made yourself desirable to her, don’t. There’s a difference between adding a dash of the language of love and full-on hitting on her.

Think about saying, “I’d really like to get to know you better” or “so many great experiences are better when shared”. And avoid anything which could come across as a practical gesture, love is not practical. Don’t say, “Hey, Wednesday is two-for-one night at the Lobster-Shack.” She might love a good deal but saving money is not romantic.

4) Start a conversation

How do you have a conversation with someone who hasn’t yet responded to your first message? It’s a lot easier than you think. Did you ever read an online article and with the first few lines have the feeling that you want to jump to the comments section? This is because the article has engaged you and a good first message does the same.

If you’ve read in her profile that she loves hiking, start by mentioning that you’re currently planning a trip to Yosemite. That way, if she’s been, she’ll feel the urge to give you some tips and pointers. If she’s a cocktail lover, talk about your ongoing quest to find your city’s best Martini.

These are the type of comments, which make people want to jump in and answer. This is how conversations start and how you get replies.

5) Be specific about wanting to meet her

Once you’ve introduced yourself, given her a compliment and started the romantic conversation, it’s time to tell her what type of date she could expect from you. This proposal needs to include an activity – it needs to be specific.

Tell her there’s live music at your favorite bar every Friday evening and you’d love to invite her along sometime. You could also give her an alternative, like coffee in the park on a Sunday afternoon.

This may sound pretty forward — jumping the gun even — but you’re not giving her an ultimatum. You’re just telling her what she can expect from you if she responds. Older women appreciate a guy who can arrange a date. Maybe she has a full-time job or a family or both. The last thing she’s looking for is a guy who expects her to plan every date too.

However, two possible date options is enough. Don’t keep listing things you two could do together. It’ll make you look desperate and act as an information overload for her. If she’s interested, she’ll make one of the two dates work and if she really can’t, she’ll propose a different day.

6) Prompt her to ask her own questions

Some younger guys seem unable to write a message to an older woman without dotting all the i’s and crossing all the t’s. They’re so keen to get a response that they tell her everything about themselves all at once. While this is a good honest approach, most older women like the process of getting to know a younger guy. And leaving her planted question possibilities is the best way to create a room for a natural back and forth.

For example, if you tell her you attend a certain college, you might leave out what you’re studying just so she has the chance to ask. If you play sports, tell her and let her ask who you support. This also goes for travel, movies and reading. You can tell her you go to the art-house movie theater every week and give her space to ask what type of movies you’re into.

As a general rule, finishing a message with an open question is a good way to get a response. If she writes to you with a question it means one hundred percent, she wants a reply.

7) Know what your message wants to achieve

Generally speaking, guys know when they find a woman attractive much sooner than a woman does a man. Women take in the ‘signals’, great hair, hot body, a nice smile etc. and our decision is made.

However, the attributes which make a guy attractive aren’t always so obvious. Good hair, nice smile and great personal style are also important to her, but personality plays a big role too. She wants to know you’re a nice person, interesting, intelligent and funny before she responds. To do this, she needs input – words.

Read your message through. Are you using the words she wants to hear – her signal words? For example, if she says she’s looking for an intelligent guy, then you want to come across as smart. To do this, you need to be using intelligent words and phrases. Saying, “I’m really smart! Really, really smart.” Isn’t going to convince her.

8) Focus on the positive

One of the most important things you need to remember in your message to an older woman is to stay positive.

Older guys tend to have a lot of baggage. They can be somewhat irritable and this is one of the reasons older women start dating younger guys. They’re sick and tired of grumpy, old men. So don’t be what she’s trying to get away from.

Maybe you’re tired of how superficial younger women are but don’t moan about them in your message. Focus on what you like about older women, not what you don’t like about younger ones.

Likewise, if you haven’t met anyone on the site yet, don’t write to her, betting she won’t answer the email. It’s a guaranteed way to make sure she doesn’t.

So that’s all there is to it. If you find a profile you’re interested in, sit down and put together a quality, well-structured message. There’s no guarantee you’ll get a response every time but you’ll get far more replies than you otherwise would.

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