How Long Should You Wait to Respond to an Older Woman’s First Message?

Wait! Are the Rules Different Responding to Older Women Online?

By: Jack Warren

If you’ve just received that first opening message from an older woman you might be tempted to reply immediately. Though there aren’t any rules around when to reply, doing it instantly is rarely a good idea. So, how long should you wait to respond to an older woman’s first message online??

I get it. Particularly as a guy, it’s exciting to receive that first message but therein lies the problem. See, text game can be tricky because you’re relying solely on their interpretation of what you write. None of the usual social cues, just words on a screen.

From those words comes your first impression on her.

The trouble with that initial excitement is that you want to reply instantly.

In most cases, that instant reply is going to be considered one of two things:

  1. You’re very desperate
  2. You have nothing going on in your life.

Both are red flags to any woman but particularly to an older woman.

There are a lot of nuances to communicating online that you don’t have to deal with when meeting older women looking for younger men out in the real world.

What you’re actually up to is irrelevant. All that matters is the impression you’re giving.

How long should you wait to reply?

It’s such a common conundrum that thousands of guys are searching for the answer every month. Before you starting thinking about how quickly to meet up in person you need to focus on just how long should you wait to message an older woman looking to date younger men?

Let’s take a closer look at how you should be handling it and what to be weary of.

When you’re actually free

First things first, don’t stop what you’re doing to reply. Nobody wants to be with a person that has no social life for a host of good reasons. Instead, treat these dating apps as a secondary priority.

When you genuinely have a moment spare, then go ahead and catch up on those messages. If you’re disengaging from your friends or that complex work project for a Tinder message you might want to reconsider!

Strangely it seems the busier my life gets, the more of a selling point this seems to be. I only kind of understand it but it’s a fact nonetheless.

The same applies when setting up the actual date. Rather than “I’m free every night this week,” I offer a couple of specific windows where I’m available.

It just so happens that I am busy most days so I’m legitimately restricted. Even if you’re not, it’s a better impression to be giving.

If you’re already free, give it 10 min!

Ten minutes is about the happy medium here. If you’re legitimately just sitting on the couch bored and need an arbitrary time, this is it: 10 minutes.

Ten minutes is long enough to be plausible that you have a life but not so long that you’ve had a mental breakdown.

I would say anything up to about an hour is fine if you feel like stretching it but try to keep it under a day.

Waiting too long is just as bad!

Don’t forget there are two people involved here. Both of you share some excitement and intrigue initially and it’s important to keep that going. The longer you can keep that excitement alive, the more successful the conversation and date(s) are going to go.

If you don’t respond for a week you can’t expect to have too many active conversations.

The only time I’ll get a reply after that long is from someone who rarely uses the app. In those situations, conversation takes so long that I’m the one who gets bored and moves on. In both cases waiting a week to reply to an older women offers a bad outcome.

3 Messages You May Get and How Quickly to Respond

Depending on how successful you are at building your own confidence there are a few ways this can go.

As a general rule, the first message you receive is going to fall into one of three categories. How you deal with them will differ and it may change the timing of your response as well.

The shy or casual “hello”

We’ve all received this one at some point. It usually looks something like: “hi, how’s your day going?”

While it can feel lazy, it usually turns out to be the result of uncertainty. Either she’s a little shy and unsure of what she’s doing on this app or just doesn’t know what she wants.

The best thing you can do here is be easy to talk to. If she’s shy, she’ll appreciate the easy chat. If she just isn’t sure if she wants to be dating, easy and friendly chat is hard to turn down.

Because this type of opener can feel so lazy, many guys will ignore them.

That’s a missed opportunity for those guys!
  • In my experience, if you’re a good conversationalist you can draw her out of her shell.
  • Those guys are doing you a favor by cutting down the number of conversations she has going.

While there’s no set time for these, I do tend to give them a bit longer. Not days but maybe an hour or so. If she’s just dabbling with dating apps and you go replying in 30 seconds, that’s the type of red flag she’s worried about.

Anna’s motto: Always leave them wanting more!

Women using an opener like this are also more likely to deactivate their profile often.

It feels like they’re giving the dating app a go (maybe under peer pressure?) and if they get nothing of interest they give up and move on. Consider it a relatively brief window of opportunity to show her it’s not all dick pics and pick-up lines.

The Canned Opener

There’s only one reason that anyone uses a canned opener — efficiency for bulk conversations.

They often read like any other type of scripted cold approach. Maybe a joke of some type or interesting fact. No mention of anything about you or your profile so it can be recycled for the next match.

This isn’t a bad thing at all when received from a woman. (Women hate canned openers and can tell they’re canned. Avoid sending them!)

In fact, I consider these a good, but challenging, match. More often than not, the woman, particularly an older woman, is motivated (hence the large number of conversations) and likely know what they want.

It’s a great opportunity because she’s probably going to be quite active, keeping up with the conversations that interest her. This is also where the challenge comes in.

It’s unlikely she’s only talking to you so make sure you stand out and keep her interest. In other words — don’t be boring.

If nothing else, chatting with women like this are great to hone your skills with. But do not reduce them to nothing more than a test subject.

Instead, you can probably expect quite a strong personality with clear responses. If you’re boring her, she’ll probably tell you or just go quiet. If you offend her or say something borderline, she’ll let you know very clearly. Plus, if you’re still unsure of your text game, she may inadvertently help you out.

If this does happen, try to focus on the positive element. Getting offended and starting an argument never ends positively for anyone.

The Blatant DTF

Huh?! What do you mean women can be just as down for casual sex?

Not only is it an obvious fact but apps like Tinder have made it far more socially acceptable. If casual sex is an option for you, these openers are a gift.

It’s usually wise to get onto these quite quickly. From my experience they tend to be a case of “I’m at home bored tonight, what are you up to?” . . . Not exactly something you should leave until the morning, right?

Another word of advice with this type of match too — don’t forget your manners!

No, I’m not your mother, I’m just embarrassed by the vulgar responses I’ve seen.

Being open to casual sex doesn’t mean she wants to be treated like a porn star! By all means, sexual conversation is fine here but keep it respectful

In Summary

That’s about all there really is to the topic of how long to respond to an older woman’s first message. Basically, don’t put your life on hold for a dating app and pay attention to the type of message it is.

If you feel like you’re still a little lost on how to handle these initial responses, I’d suggest trying Bumble. It’s designed so that women have to be the one to start the conversation. Even after matching, you cannot message her first. That tends to attract more of the canned opener and DTF crowd but it also means more opportunity to practice.

If you match with 10 women in a week on Bumble, you may get 7 or 8 of them message you. That’s much more opportunity to be exposed to this scenario than the 1 in 20 or so that I seem to get on Tinder. The vast majority of the time I’m the one opening.

Just like all other aspects of the dating world, delivery is the most important element. For that reason, people’s opinions do vary on the topic. What do you think? Do you have a specific time that you wait before responding?


AJ Notes:

Let us know how long you usually wait to respond to an older woman’s message and how that’s worked for you! In fact, let us know how long you wait to respond to any woman’s message.

Have a specific topic you want us to write about? Write it in the comments!

Just want to get your ass an amazing girlfriend, older or not? Hello! Check out how I can help you: Click here!

About the Author Anna Jorgensen

Vancouver Matchmaker and Dating, Love and Relationship Expert Founder: Wingmam

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