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Should You Message an Older Woman a Second Time if She Doesn’t Respond?

Note: This is a sponsored post for, written by Keenan Cruz

One of the drawbacks to dating apps is the mental aspect. Unless the conversation is rolling quickly, we spend so much time in our own heads. Agonizing over the details, wondering what she meant by that phrase or what she’s up to.

Perhaps the hardest one to figure out is what to do if she doesn’t reply. Do you just leave her be and move on? Should you send another message “just in case”? It’s a difficult one because emotions can get in the way, so let’s take an objective look at it.

To message or not to message, that is the question

Ultimately the answer here depends on the method of communication. There are different expectations and possibilities depending on how you’re chatting up an older woman looking for younger men. Let’s take a closer look at each of these below assuming you have already done the work in properly building your digital dating presence.

Dating apps

With apps like Tinder and Bumble, a big part of the attraction is relative anonymity. Sure, your name and photos are there but if you unmatch someone that’s the end of it.

This tends to bring with it the expectation of low commitment from both parties. If you’re busy and don’t have time to reply until tomorrow that’s absolutely fine. Likewise, if you don’t feel like talking to a match anymore, there’s no expectation you continue. Nobody should be offended by this, it’s just how the apps work.

Of course she has the right to do exactly the same without repercussion. If you don’t receive a response from her after a particular message, my advice would be to leave it alone. Move on to someone/something else and let her be. Even if you could wrangle a bit more conversation, is that really what you want? To draw out chatter from someone disinterested?

If it’s a match you were particularly interested in, the voice in your head may be trying to convince you otherwise. I’ve been there. The self-doubt makes you wonder “what if she’s just busy and forgot to reply?” “If I send her a quick message, maybe that’ll remind her.”

Maybe that voice is right but unfortunately, it’s unlikely. Perhaps spend a little time seeing where you could have improved, if anywhere. Sometimes people just don’t click and that’s okay.

All of this is especially true if you’re early in conversation. If there have only been a few messages back and forth and there’s been no reply, move on.

Dating websites

Most dating websites focus more on the pursuit of long-term relationships than a quick fling. This changes some of the rules and expectations but not when it comes to when a woman stops responding.

You may be able to get away with a brief follow-up message since users can be a little less blasé about the whole thing. With that said, my advice is no different here — leave it be and move on to something else.

First though, you have to make sure you are only spending time on the top rated dating sites for meeting cougars. Luckily we’ve done the homework for you on that front.

Text messages

It doesn’t matter if you’ve successfully escalated from Tinder to text message or exchanged numbers at the bar. Either way, once you’ve reached this stage you can consider it a sign of mild commitment.

This doesn’t mean you necessarily owe each other anything but expectations do change. By this point you already know a bit about each other and have decided there’s mutual interest.

From this point on I find conversation to be much easier. First impressions are already made, I have a clear sign of interest and I can relax a little more. It also means that if she decides she isn’t interested, she’s most likely going to tell me.

What that means is getting no response now is more likely to be because she’s busy than flat out disinterested. If it’s been a day or two without a reply, go ahead and follow up with another message. Be sure to keep it short and for everyone’s sake, if you get no response from the second message — move on.

Think about it this way. Maybe she’s just away on vacation or broke her phone. If she goes to reply a week later and sees 17 pleading messages, you’re making the “crazy clinger” category. No more than two messages!

Dating agency

If you’re the dating-agency type, the advice can vary a little depending on the setup. Since every agency runs slightly different, it’ll depend on how you communicate with your dates.

When it’s through their website, then the “Dating Apps” section above applies to you. When you’re given a number or exchange them after a date, the section above is going to be the most applicable.

As I mentioned in the beginning, how you handle these situations depends on the method of communication. Exactly how you came to make the connection is far less important.

After a date

I’ll be honest. If you had your first date a few days ago and she’s ignored you since then, it’s not a good sign and you may not have followed our advice for meeting an online connection for the first time. Unless you know she had exams or something going on and would be busy, I’d probably leave this one alone.

The reason she isn’t responding can be hard to determine sometimes. Whatever the reason, don’t beat yourself up about it. Maybe you did say or do something questionable but it’s just as likely she went back to her ex or something.

Trying to figure out what you did wrong isn’t particularly constructive since the answer may be “nothing.” Instead, take advantage of the world we live in. A few more swipes and you’ll have a fresh match, right?

Repeated slow responses

A slow reply here and there is nothing to even analyze. You’re busy, she’s busy and neither of you deserve to feel bad about it. With that said, if you’re texting each other and she takes days to reply every time (with no valid reason in sight), that’s a little different.

Think about the match you were most into. Now think about how excited and eager you were to reply to her. As your interest in someone wanes, so too will the urgency in your replies.

It’s no different for her. Once again, it’s not something to beat yourself up about. The cause may have absolutely nothing to do with you. That doesn’t change the fact very slow replies to every message is a sign she’s just not that keen.

Calling her on it really won’t achieve anything constructive. Instead, I tend to leave the ball in their court if this happens and move on.

For example, I might send her a message like:

“Hey Sarah, I’m away for the weekend but have a few nights free next week. Let me know if you want to go do something through the week”.

She may reply with a rather generic “okay, sounds good” and that’s fine but I’ll leave it there. Now, if I’m reading it wrong and she is keen, she’ll text me. If not, that’s fine too. It’s an easy, low-pressure out for her and it means I’m not trying to carry a reluctant conversation.

How to follow up with a second message

If you’re going to send her a second message, then it’s important you do it the right way. The impression you make is crucial and you don’t want to come across as needy.

First off, as I mentioned above, you want to limit it to one follow-up message and then leave it alone. A daily message for two weeks screams an epic degree of neediness.

Perhaps more importantly, don’t go making her feel bad. Although it might be frustrating to receive no reply, she hasn’t done anything wrong. Choosing not to continue a conversation is her right, as it is yours. You may want to hold her accountable in some way but all it’s going to achieve is making her feel bad. Instead, try to be a little more respectful and just let it go.

Think about it this way, what if she was likely to get in touch with you again in the future? If you made her feel bad about your last interaction do you think she’ll want to go there again? Probably not.

So much of this topic is about patience and mental discipline. In the excitement of meeting someone you really like, it can be hard to wait for a response. It can also be crushing if you don’t get a reply at all.

Whatever happens, remember you’re both complex individuals. You each have a lot going on and slow/no reply isn’t necessarily a reflection on you. Be respectful to both yourself and her and things will be that much easier. You might be surprised who comes back down the track with an explanation.