5 Online Dating Message Tips Proven To Get You A Date With An Older Woman

A lot of guys make a number of mistakes when trying to get attention messaging older women. But with these five online dating message tips, you won't be one of them.

Online dating message tips often miss the mark. That’s because while they might get a potential lady to respond to you, you want more than just a response. You want a response that will continue to create interaction. “Yes” and “no” are certainly responses but they don’t get you much further than where you started.

If you want to make a successful online connection with an awesome lady you need to know how to make your messages count. These online message tips are proven to help you get a date with an older woman and they apply to younger women as well.

Online dating message tips destined to work

Older women aren’t nearly as easily charmed by being “liked” or “favorited” or any of those other prefab mechanisms designed to show interest. You’ve got to bring an ‘A game’ to online dating when it comes to women with experience. They’re a harder sell because they have so much more to offer.

These five online dating message tips are great for upping your online dating game in general. Learn how to use these online dating message tips to improve your e-dating life as well as meeting people in person.

1)  “Winking” is not a message but it sure sends a message

Online dating apps and sites all have some type of generic way of indicating interest. These sites suggest all you need to do is “let her know you’re interested.” It certainly helps if you are using a high-quality dating site as well. If you are interested in meeting attractive older women we have put together a great list of the top dating sites for cougars.

Smiles, winks, nudges, favorites, likes, taps, flirts, swipes . . . They all require zero effort or thought. In fact, these are so easy you’ve probably accidentally swiped or liked someone you didn’t intend to on more than one occasion. Older women know their value and they’re unlikely to respond much less be interested in a gesture that everyone knows is virtually meaningless.

The problem with the generic wink, etc. is that . . . well, it’s generic. How much interest does that actually convey?

The wink-type message is obviously designed to casually test the waters and indicate preliminary interest. The hope is that the other party will then reciprocate and so on.

However, because these mechanisms require no thought or effort most women are numb to them and completely disregard these outreaches. Some women assume that these indicate laziness and boredom-induced swiping, neither of which are appealing.

2) “Hi there, great _______” is a dead-end message

Okay, so you’ve observed something about her profile or pictures. So what? When you send this type of message the only thing you are conveying is that you have a keen grasp on the obvious. If you are still struggling with your overall ability with women there are some books you need to check out that can help.

That’s not a point of interest for any woman much less an older woman with sophistication. Are you expecting her to be flattered that you took a valuable 90 seconds to look at her pictures or skim her profile? Seriously . . . Why would she be flattered by that? How does that differentiate you from everyone else who messaged her the same thing?

Online dating message tips proven to get you a date with an older woman are focused on separating you from the herd as well as recognizing her as a unique individual. You want to be appropriate without being mundane. So at least find a personalized way of pointing out the obvious.

Let’s look at some possibilities for a woman with a yoga picture in her profile.

“Hi, you’re into yoga?” or “Hi there, nice tree pose”

This message idea is generally on track because it shows interest in something she’s got going on. However, it is also a total dead-end message.  It’s an invitation to the obvious and dead-end response, “yes” — and an unnecessary statement of the obvious.

Here are some better variations. They’re still appropriate and demonstrate interest in her specifics, and they also open the door for more dialogue and conversation. In doing so, you demonstrate interest in her as a person beyond what is already obvious in her profile.

  • “Hi, I see you do some yoga. I’ve been thinking about trying it. How did you get started and what’s it been like?”
  • “Your tree pose is solid. Mine is not so solid. 😉 What type of yoga are you into and what do you like about it?”
  • “Tell me about your yoga experience . . . I know people do it for all kinds of reasons. What are yours?”

When you send a message that opens up more dialogue you are indicating interest in the person beyond the profile. Older women recognize that as a sign of the intelligence, sophistication and maturity they seek in social connections with men.

3) “Hi there, you seem ________” is a really painful message

This type of message has multiple red flags for women:

  • It suggests you’re suspicious i.e. insecure.

Using the word “seem” implicitly suggests you have some reservations as to the reality of what you are seeing. This makes you look insecure. It conveys that you are already seeking reassurance before you extend yourself any further. That’s a no-go.\

  • It suggests you’re arrogant.

“You seem [cool/interesting/fascinating/fun]” suggests that this woman should jump to reassuring you that she is, in fact, what she “seems” so as not to lose your potential interest. Wrong!

No woman is going for that, especially not an older woman who knows her worth. Also, it in no way says anything compelling about you. It does suggest you think the woman should prove herself awesome before you lift a finger.

  • It suggests you’re a one-sided conversation partner, if that.

A statement of observation without an invitation for more dialogue tells an older woman that you like to hear yourself talk and don’t care much about actual input from the other person. ‘Nuff said.

The point of messaging a woman is to get something going. So do yourself a huge favor and make sure you’re not sending messages that bring conversations to a stop before they even get started.

4) If a message is meant to show interest, then make sure it shows meaningful, specific interest

A million billion people on dating apps enjoy the same things. That’s okay. But mutual interest in “The Office” is not a reason to get a conversation going. It’s definitely not a reason for an older woman to meet up with you (all her friends like “The Office” and hiking and cocktails, too, guaranteed).

Using a common interest is a good starting point, but you have to expand on it. Let’s use the example of the show “The Office” as a common interest and see how to expand it to something more compelling that doesn’t come off as generic as a “wink”:

  • Hi. “The Office” is the best, right? I tried “Parks & Rec” but nothing’s the same without Dwight. What are some other shows that you’ve enjoyed? Do you ever like thrillers? I’ve been watching “The Wire” and it’s incredible.
  • I’m in total withdrawal since “The Office” ended. Seriously. I’m not a huge TV watcher, but I couldn’t believe how I got sucked into that show. How about you? Or are you a serial binge watcher? 😉
  • Steve Carell is the best. THE BEST. Have you seen any of his dramatic roles? Quite a departure from Michael.

The idea is to use the stated information as a starting point for more conversation. Otherwise, you come across as having limited ability, interest, or energy to engage her beyond the contents of her 150 word profile, and she isn’t going to put any effort into you either

5) Messaging is kind of an audition, but not just hers

There’s an important line between being interested in her and cross-examining her.

Yes, you have standards and they’re important. She does as well. Especially if you’re coming off a breakup or burn, be aware that defensiveness comes through messages loud and clear as interrogation. No one – including you—is likely to respond well to feeling like they are being vetted. Similarly, your questions say a lot about you.

One of the most important online dating message tips is to be aware of how you come across.

  • Make sure each message you send has at least one question mark in it somewhere.

Messages that don’t invite dialogue by asking for some sort of response say that you aren’t really interested in getting a response.  That’s a deal breaker for quality women.

  • Make sure your questions don’t invite “yes” or “no” answers.

Questions that elicit a “yes” or “no” response are just as useless for engaging someone as no questions at all.

  • Read your messages out loud to yourself (or even better, someone else) before you send them.

Sometimes it’s hard to know what we sound like to another person unless we test drive it. An innocent inquiry might accidentally sound demanding or pushy without you realizing it. Try test driving this stuff with a friend before you send it.

  • In the early stages of e-communication, do not bring up questions about their most recent dating history, etc.

Older women have many more interesting things to talk about than their romantic life prior to you. If there’s something going on, you’ll find out about it soon enough. Questions like, “So is that your ex in the boat pic?” or “How long have you been divorced?” will make you seem really boring and more than a little insecure.


These online dating message tips will help you make connections with quality women and keep them going. When you use these tips as guidelines in your e-messaging you’ll find that you make more quality connections and waste less of your time on superficial interactions that aren’t going anywhere anyway.

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