11 Things to Remember Before You Message an Older Woman Online

So, are you ready to dive into 11 tips for messaging an older woman online? Keep reading.

Don’t try to be something you’re not

As a younger guy, you may be tempted to lie to impress her. You know, make yourself seem older, wiser, and more worldly. You want her to know that you have interesting things to offer. But if this persona you’ve built isn’t real, it’s going to be hard to keep up and it’s bound to dissolve at one point or another.

Do it right: Don’t overlook the very real assets you already bring to the table. She will like you precisely for your youth, fun demeanor, and the breath of fresh air you bring to the relationship. Play those up and forget about trying to seem older. Your youth is a feature, not a bug!

Tailor your approach

It’s good to keep in mind that an older woman socializes differently than, say, a girl in her 20s. That doesn’t mean you have to be a different person, just tailor your message to your audience. Whereas you might begin the conversation with a pick-up line, an emoji, or a reference to a meme with a girl your own age, you have to speak to a mature woman in a social language that she’ll understand. Otherwise, she might feel old or inadequate.

Do it right: Being playful is certainly a quality she’ll enjoy in a younger man. Make her laugh, tease her, be flirty, etc., just be respectful, don’t play games and remember to spell out your words. I’d be careful not to use too many acronyms or “hip” new terms that can even make 25 year-olds feel old. If you are having trouble building up the confidence to send that first message check out some tips here on overcoming that anxiety.

Make sure you are looking in the right places

Finding a single, attractive older woman isn’t always an easy proposition. You need to be smart about where you are looking or you can end up wasting a lot of your time. Make sure you are using a legitimate dating site with a lot of single older women.
Do it right: It can be hard to tell the good sites from the bad so every year we put together a complete cougar dating website review to help younger guys with just this problem. Be sure you are using a site that has a free trial offer before you commit any of your own money. If you are on a site that demands up-front payment before you have a chance to check it out you should run away fast!

Read her profile and look at her photos

Some men will message a woman with something like “What are you doing this weekend?”, or “What’s up?”. But that approach is a tad impersonal. Also, it doesn’t really require any effort at all, does it? An older woman wants to be complemented, wowed, but most important of all – listened to. The one-size-fits-all message isn’t for her. But how can you grab her attention and make her feel special?

Do it right: Reference a few things from her profile, so she knows you’ve been paying attention. If you want to compliment her, don’t make it about her appearance. Look at her photos and pick . It could be related to a hobby, an accomplishment, her family, etc. She’ll appreciate that you demonstrate depth and are interested in something other than her body.

Don’t be intimidated by her possible experience

The thing with older partners is that they may be more experienced. Some people like that, but others can be intimidated by it. She may have you beat in number of partners or range of experience, because hey, she’s had time to practice. Or maybe that’s just your perception. Who knows, if she’s been married her whole life or hasn’t been particularly experimental, you may be able to teach her a thing or two.

Do it right: Don’t let her history stop you from messaging her, because then you both miss out. It might turn out that she does have more experience. But, that only means that you can learn something new from her. Instead of feeling inferior or intimidated, revel in her knowledge and allow yourself to be taught. It can be incredibly sexy.

Don’t automatically assume she’s after something serious

You may be tempted to think that because she’s older, then that means she’s after marriage, a baby daddy, or a father figure for her children. But you’d be wrong to stereotype. Just like younger women, older women look for all kinds of things from relationships. Some will seek stability, sure, but others will be looking for a fling.

Do it right: Before you message anyone on an online dating site, it’s always best to take a good look at her profile. Most will state outright that they’re only looking for hook-ups, or on the contrary, someone serious to settle down with. Pick accordingly.

Don’t fetishize her age

I shouldn’t need to say this, but your age or hers shouldn’t come into play, especially when you first message her. Do you really want her to think the first thing you noticed about her is that she’s older? That will only make her feel self-conscious. You’re two people that have stuff in common and may like each other. What does age have to do with it?

Do it right: You want her to know that you’re attracted to her sense of humor, your shared interests, her beauty – but mentioning your age gap is just unnecessary and perhaps even uncomfortable, depending on how you frame it.
Extra tip: don’t use the word “cougar”.

Talk about her, not yourself

I get it, talking about yourself is an easy trap to fall in. However, sending a message that’s all about you might make you look a bit self-centred. You want to show her that you’re interested in her, getting to know her better, and fostering a possible connection between the two of you. Show her the younger generation is different than the men she’s used to and open to understanding her needs.

Do it right: Crafting the perfect first message hinges on a delicate balance between expressing interest, demonstrating compatibility, and sharing a bit of information about yourself, to intrigue her. Let’s say you both like Game of Thrones: “Hey, what GoT character would you be and why? I’d like to be Stannis Baratheon because I think he’s honorable and fair and that’s something I appreciate in people. Maybe we could talk about it sometime, I think we’d get along.” You can find a more in-depth guide on starting a conversation with a girl. The guide is geared more toward texting but still applies for online messaging.

Highlight your shared interests, not the differences

What stops older women from going for younger guys a lot of the time is the fact that they believe that they’re in two different places in life. That’s why it’s your job to focus on what you have in common when messaging her. Don’t draw attention to differences, especially if they’re not a deal-breaker for you.

Do it right: Express how glad you are to have found someone so compatible. Talk about everything you have in common. Tell her how exciting she is and convince her that you really don’t mind the occasional differences in lifestyle. On the contrary; you’re happy to learn more about her and these differences are what make her fascinating.

A wall of text might overwhelm her

Look, you don’t want to just write “Sup?”, but a 500-word declaration of admiration will come across the wrong way, too. You don’t want her to feel like you’ve been “studying” her for that long and spent an hour telling her your every thought and feeling about every aspect of her person. Write the Goldilocks of messages: not too short, not too long – just right.

Do it right: Ideally, you would write a few sentences, say 4 or 5; about a paragraph. That gives you enough room to talk about her interests, or any interests you share and then ask her a question, so that you keep the conversation going. Always pass the ball back in her court at the end of a message.

Don’t gross her out with sex jokes and innuendos

Even when all you’re looking for is sex, it’s never wise to start with an unsolicited nude pic, a crude joke, or some pervy comment. I can tell you now that no woman appreciates that, especially a mature one. She will not be flattered by your overt sexual references; she will be put off by them.

Do it right: Real flirting is so much more subtle and sensuous. Sexiness is hidden in hints and allusions that make her imagination go wild. If you just come and say it outright in the perviest way possible, the magic is gone and it’s replaced by repulsion.

In the end, dating an older woman – online or otherwise – is not actually that different, but you do need to think more carefully about your moves, from the very first message to the first time you take her out. Remember to treat her with respect, tailor your approach to her expectations and don’t let the age gap get in the way of romance. Good luck!