5 Great Questions To Ask An Older Woman In Your First Online Dating Message

Would you like to date an older woman? Read this contributed post to make your online dating messages grab her attention.
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The beautiful thing about dating apps is you know there’s mutual interest before the conversation even starts. So why do so many guys complain about how impossible they are because women don’t respond? It’s simple — they’re doing it wrong.

That’s great for you because we’re about to go through how to do it right. I’ll also cover a few examples you can use and adapt.

Getting the conversation started 

According to Tinder Seduction’s study, just 50 percent of guys will message their Tinder matches. Only 14 percent will say anything beyond “hey” or “hi.” For the mathematicians out there, that’s 86 percent of guys saying literally nothing constructive to women on Tinder. Starting to see the problem?

You could literally head-but your phone keyboard, hit send and put yourself in the top 50% of male Tinder users. Maybe don’t consider that tip #1 though.

Before we get onto specific question openers, let’s take a moment to cover the essentials.

Essential ground rules to remember

Do your homework

Before you go saying anything, take a quick look at her profile. So long as she’s got more than a single photo in there, it should tell you quite a bit. You can get an idea of what she likes and the type of person she is.

Accomplished business woman? Regular socialite? Alternative style or living the vegan life? These factors should play into your opening message. Spending 10 seconds actually reading what she has to say and checking out her photos will go a long way.

Watch your spelling and grammar

Particularly with older women looking to date a younger man, you need to keep an eye on this one. Being on the older end of the Millennial age bracket, I have a number of friends that qualify as “older women.” I can tell you right now unless you’re Zac Efron, constantly mixing up your/you’re is getting you ignored.

It sounds trivial but what it’s doing is promoting the idea that you’re uneducated or lazy. Untrue as that may be, she only has a handful of words to judge you by. Make sure your English teacher would approve.

Start with her name

If you’ve ever picked up a sales and marketing book, this is something you’ve likely read about. That’s because, in short, hearing our own name activates the brain in a positive way.
It also demonstrates you haven’t just copy/pasted that first message to 20 women.

Now this doesn’t mean you have to open in a formal manner. In fact, one of my favorite dad jokes starts with a question. The first word I use is their name:

“Hannah, I have a question for you. What does. . .”

Short, fun, flirtatious

The purpose of the opener is to do just that. You’re not trying to do anything beyond starting a positive conversation with her. The rest will come later.

The way we interact with these great cougar dating sites  and apps is much the same as we do social media. All we’re interested in reading are tiny morsels of information, then we move on. “Oh look, Jane has written another 500 word Facebook status . . .” [keeps scrolling].

I’ve received lengthy messages from women in the past and even I’m guilty of it. I saw the message take up more than my entire screen, started reading and closed the app. If my attention span is that short, imagine how women will respond when they have an abundance of matches?

This leads me to my next point . . .

Don’t be boring

If you look at the study mentioned above, you’ll see that 36 percent of the male matches just opened with a greeting; “hey”, “hi” etc. Yawn.

Granted, saying “hi” is an improvement on total silence but it’s hardly stimulating. You want her to feel engaged in the conversation with a reason to respond.


On to the questions

Questions are such a great way to open. They’re giving her such an easy entry into the conversation since all she has to do is answer it.

There are a few different themes you can choose from here depending on your personality and hers.

Focus on her exciting memories and achievements

No matter the context or medium, the easiest way to keep a conversation going is to have her talk about her. She’s the most interesting person in her life — That goes for each of us.

That means talking about her positive experiences is going to be that much more engaging. It’s also allowing some positive association with you, too.

Here are some examples. Be sure to link them in with what you observe from her profile — if it’s relevant.

“That’s an impressive collection of travel pics. What’s your favorite memory from your travels?”

“Pretty sure I’ve climbed that mountain. Is that in Utah?”

“Captain Emma, huh? Very impressive. How long have you been a commercial pilot?”

“I’m actually planning a trip to Spain for August. Was it amazing as the photos make it out to be?”

“A fellow traveler I see. If you could be anywhere in the world right now, where would it be?”

Serious questions on silly topics

These are all about the cheap laugh. There’s no easier way to start a fun conversation than to begin it with a laugh, right?

“I think we’re at that point in our relationship where I have to ask you a very serious question. . . plain or peanut M&M’s?”

My favorite matches are the ones that let this question devolve into an entire, faux-heated debate over why peanut M&M’s are (obviously) better.

The mini quiz

The concept for this one is simple and entirely re-usable. Create some type of multiple choice question. You’d be surprised just how effective it is!

“Hello and welcome to Ash’s quiz show. The game is simple. Below are two facts and a lie about me. Choose the right one and you’re a step closer to the coveted first date!

1. I have a legitimate man crush on Harvey Specter

2. I grew up on an Ostrich farm

3. I speak fluent French but am always too embarrassed to use it
    
Choose wisely!”

In case you’re wondering, #3 is the lie. My French is terrible! Naturally, conversation comes easy off the back of this, even though most get it wrong.

Truth or dare

Does this question even need an explanation? Be sure to have a few responses lined up for whichever option she chooses.

The reason this kind of works is that it’s such a cliche that it’s ironically fun. It also lends itself well to turning the conversation more sexual quickly if she seems the type.

Dad jokes

A personal favorite of mine and a go-to for blank profiles. Again, designed for the cheap laugh to get the conversation started.

Bonus points when these dad jokes are followed up with a relevant gif.

Here’s a recent exchange I had with my favorite dad joke/gif combo:

Me: “I have an important question for you. How does a penguin build his house?”

Her: “Do they even live in houses?”

Me: “Of course they do! You think they stay looking that sharp sleeping outside?”

Her: “Haha well played. Okay, I have no idea.”
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Me: “Igloos it together!”
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via GIPHY

Image copyright HIT Entertainment Ltd.

Her: “omg I love Pingu! Okay, want to set the wedding date now or should we pretend to play it cool? Also, that joke was terrible. I’m impressed.”

One word of caution here though. Some women just don’t appreciate that type of humor so be sure to have something up your sleeve.
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A matching sense of humor is very high on my priority list, so I’m okay with letting the flat responses slide. If you do want to pursue it though, consider it a fresh conversation. Choose another, more match-appropriate opening and try again.


The thing about openers is the good ones can rarely be reused. The examples given above will give you some inspiration to get you started. From there, pay a little attention to her profile and get creative. Remember that nobody wants to feel like just a number. Opening with some type of reference to her profile is a great way to demonstrate genuine interest.

While dating apps are a numbers game to some extent, try to avoid that attitude. Instead, spend a little time selecting women you’re truly interested in. It goes a long way and you’ll have a much better time doing it.
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Humour and wit are widely appreciated and quite easy once you get the hang of it. Go ahead, try out some of the examples above and let me know what else you come up with.