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How to Write a First Online Dating Message That Will Impress an Older Woman

It doesn’t matter how experienced you are at dating, the rules are always different when you’re dating a MILF. An older woman has been around the block a few times, and she probably hasn’t got time for games and protracted communications.

Young cub texting an older woman
Wit and humour are always effective at attracting the attention of an older lady

She is able to separate the genuine guys from the players, which means you need to impress her from the off — and the best way to start is to write an engaging, concise and upbeat first message.

Dating sites are full of men looking for older women, so it’s important to get the wording of your initial introductory message just right. To help you get started on the journey towards successful mature dating, here are a few message writing tips.

Don’t include anything about physical appearance

Mature women are absolutely inundated with messages from horny men on online dating sites. Many of these messages include requests for photos and details of breast size etc.

The average woman will be used to this situation, and she will simply delete any message that starts with anything relating to her physical appearance. Don’t even compliment her on her appearance; instead, ask about her likes, dislikes and general outlook on dating.

Don’t say hi or hello

Once again, it’s important to make your first online dating message stand out from the dozens of others competing for attention. As most of these messages will be one-liners beginning with “hello” or “hi’, it’s probably best to avoid them altogether. Instead, start off with an interesting and quirky fact about yourself. Wit and humour are always effective at attracting the attention of an older lady.

PRO TIP: A great way to start your initial message is to ask a question, based on the information in the woman’s biography. Demonstrating that you’ve taken the time to read it could create a great first impression.

Talk about shared interests

Read the woman’s profile information carefully, and choose an interest that you share. This will give you some common ground from which to strike up a conversation. It might be something relatively trivial like movies or walking dogs, but it could be the issue that tweaks her interest.

And let’s face it: it’s always easier to get a conversation going if you both have something in common.

Dial down the confidence

The last impression you want to create in your initial online dating message is that you’re arrogant or narcissistic. Don’t be afraid to make fun of yourself a little, and don’t talk about your own appearance.

PRO TIP: Talk about how unlucky in love you’ve been, and how hard you’ve tried to find a companion. For an older woman, this could prove very endearing.

Include your name and contact details

An older woman often doesn’t have time to beat about the bush when it comes to getting to know a younger guy. She’s wasted too much time on previous relationships, and she wants to make the best possible use of the years she has left.

If you’re confident that you both have enough in common to sustain the early stages of a relationship, include your name and some contact information. Who knows… she might just be impressed with your confidence.

Make it all about her

The last thing you should be doing is talking at length about yourself during that initial message. Instead, raise a question or a general point based on her profile information. For instance, you might notice that she’s into football, so you could start by asking her what her favourite team is.

Alternatively, you can ask her to tell you more about her love of horse riding: what does it involve? How do you get started? This will show that you are serious about looking for a relationship, and not just after a no-strings quickie.

The important thing to remember when writing that first online dating message is to be genuine. Show genuine interest in the cougar that has attracted your attention, and be genuine about your own likes and dislikes. Most importantly, show respect and kindness — and you should be able to look forward to a very successful first date.

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