Should I Text Him Again? We had Such Fun Conversations!

“Should I text him again?” is one of the most frequent questions single women ask. The answer depends on how many times you’ve already initiated texting. Learn what’s most effective.

should I text him again
Should I Text Him Again?

Can I Text Him Again? I’m So Tempted

“Dear Dating Coach Ronnie,

I met a guy online two weeks ago and we immediately exchanged numbers to talk on the phone. Had a great conversation with a lot in common and talked for nearly two hours! Then we talked again the next night for almost another two hours and discussed meeting in person sometime, perhaps for lunch, coffee, or even the dog park since we are both dog lovers.

I said that would be great and told him my availability. It was a Friday night so figured that weekend was probably too soon to plan something since he didn’t set a date, but thought I’d at least hear from him the following week. Haven’t heard from him since.

I decided to text him on Super Bowl Sunday (9 days after our last conversation) to wish his team well and said “hope you’re doing well!”. No response. Bummer

I’m confused because of how well we hit it off on the phone and he knows I’m interested. Should I text him again in case he didn’t get my text? Or chalk it up to him not being that interested, which again just boggles my mind because of how well our conversations went.

I also wonder if he is waiting until after Valentine’s Day since I assume this weekend will be a lot of couples going out and guys seem to be a little weird about that day. I’m tempted to text him again and suggest getting together for coffee or meeting at the dog park.

This would be the perfect weekend to meet since my kids are with their dad this weekend. But I just not sure what to do.

Please help!
Ready to Text


Dear Ready to Text,

I know this is hard and it seems like it should be so simple. You wonder why you need to agonize over “Should I text him again?” But that’s your tip off it’s not the way to go. You are right about that!

Even though its so temping to text him again, DON’T DO IT!

See, if this man was truly interested, he would be still talking to you. He would have scheduled a date and shown up. He would have asked you out again.

The fact that nine days have gone by since your last conversation can only mean one thing and I say this with a compassionate heart – HE’S NOT INTO YOU.

Yes, you had two great conversations. Yes he knows you are into him. But you can see that’s not enough. He has to WANT to take that next step to meet you. Even if you did text him again, do you think that would do the trick and get him interested again? I doubt it. He knows exactly what he has to do to see you. AND HE’S NOT DOING IT.

I’m not saying this to be mean. I want you to understand how men think so you stop wanting to text a man who is not interested. One of my specialties in dating over 40 is helping single women with understanding men. How men think. Why they behave the way they do. Revealing what is really going on.

So what is going on with this man?

  • He might have met someone else
  • He’s distracted by several women
  • He got busy with work
  • He’s not serious about dating or finding love
  • He’s just looking for an ego boost
  • He might love talking on the phone

Sometimes all a guy is looking for is a friendly female to talk to. You had a great conversation and now he feels confident about attracting a woman like you. So he’s all set and ready to move on. Or any number of other possibilities. And it has nothing to do with Valentine’s Day.

But one thing you know for sure from his behavior is you have fallen off his radar. And that wouldn’t happen if he was interested. Which is why texting him will NOT get him back on that track. Even if he texts you back.

Adult Dating Should Be Easier

But it’s not. I know it seems you should be able to just speak directly about simple things like setting up a date. But age doesn’t change the dating game because it’s a mating ritual rooted in biology.

A man’s DNA is coded to hunt and pursue. That has not changed. So to be successful at dating, you have to live with the fact that you choose from the men who pursue you. If you pursue men, most will run – read this post to learn more. It doesn’t work.

So what’s a midlife single gal to do? Well the answer to, “Should I text him again?” is no.

You can be friendly to get a man’s attention – then he may decide to pursue. Women are not powerless! That’s what flirting is all about. You have plenty of power – the power of allure. Learn to use that. You can’t turn every man’s head but you’ll get your fair share of attention when you rely on your feminine charm.

Then know not to read into situations. They have to play out and if the pursuit is not consistent, know then to walk away with dignity. You deserve a man who knows you are a great catch and does what it takes to win you over.

My dating advice for you is not to read into a conversation has indicating anything. If it was fun – good enjoy it. Just realize the only thing that matters is did the man ask you out? If not, stop talking to him after seven days and move on. This way you’ll be assured of not holding out or wasting time waiting around for a man who has not proved his interest.

This applies to texting, emailing, talking on the phone, facetime, social media and even flirting. If you feel there might be something there then wait two weeks if you must, but never more. And two weeks is really one week too long.

Okay, now get back out there – there are so many men to meet and the right one is waiting for you.

Wishing you love,

should I text him again

Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

6 thoughts on “Should I Text Him Again? We had Such Fun Conversations!”

  1. Hi Ronnie, I’ve been overanalysing this situation for too long. If a guy asks me vaguely out, such as “would you like to meet some day? :)”, what is the encouraging answer a lady can give so that the man will still remain the hunter and pursuer?

    I’m asking this question because this one guy asked me this question through text and I answered with “Sure, let’s just see that both of us can.” He did not set up a date. I’m starting to regret that my answer was too weak and he took it as a no. What do you think of this as well?

    • Hi Erica, Your answer was not weak and do not blame his lack of leadership and initiative on yourself! If you want a way to respond that might leads to a date with a guy who asks if you’d like to meet someday, you can ask, “Sure what did you have in mind?” Now he’ll either pick a day or say he’ll get back to you. A man who doesn’t set the date is NOT SERIOUS so move. You want a man with initiative who WANTS to get to know you face-to-face. That makes this guy the WRONG man for you. Yes, it is that simple. Don’t let your “love tank” drain because men like this who string you along. Keep yourself fresh for the men who know they want love now by moving on and sometimes even blocking them.

  2. Hello, I have been talking with a man for 2 months! He likes me and I like him. We talk often (every 1 -3 days depending). Its clear we both want just sex! He’s not ready for a relationship right now and this is ok for me too. He proposed to meet in my house! I felt very uncomfortable, so I said first we meet outside even for 10 15 minutes. He didn’t want to do this and he said he’ll wait until I’m comfortable. I looked into him and his life and everything is fine, so I agreed to meet in my house! He just answered “Its impossible this week”. I’m furious! I texted “ok baby, hope everything is fine” (trying to be cool) and then nothing . He hasn’t texted me 3 days now. I decided not to press him but I really do not know what to do. I am a “special girl” meaning I have a disability and he knows and he is ok with it. I really do not want to loose that chance. What is your advice? Many thanks in advance!

    • Hi Jennifer – I’m nervous for you because of this idea. You can only do so much research on the internet – you’ve got to meet a man before you have sex with him. You just never know at your safety is at stake. As far as this man is concerned – he just wanted to talk about sex, not have it or he would have come to your house. There are plenty of men who “cheat” on wives or girlfriends with virtual relationships to give them the variety and attention they crave without actually cheating. So you have not missed out on anything with this man. There’s nothing wrong with casual sex if that is your goal, but PLEASE be smart about it and at least meet the men in a public place first.

  3. Hi Ronnie,

    I met a man online who I’ve been seeing at least once a week for the past 5 weeks. Everything seemed to be going great, and seemed to be getting more serious. He’s had me say hello to his mother on the phone, and introduced me to one of his sisters in person. On our last date, he even spoke to my mother on the phone and took it upon himself to offer to come to her house with me for a weekend (3 1/2 hours away) to help her out with something. Before I left that night (Monday), he asked when he would see me again, and we agreed upon Saturday during the day as he had a retirement party that evening. We were in regular communication through the week, and a little more than usual. On Friday I texted him to see what the plan was for Saturday. He said he had to go to Brooklyn to help with something in the afternoon (his sister lives there so I assumed it was for her), and he asked if we could reschedule for Sunday, which I agreed to. He said he’s come to my place so I asked him to let me know what time to expect him and he said he’d keep me updated. I didn’t hear from him, so around noon on Sunday I texted him to ask what the plan was. He didn’t respond until almost 2:30, and when he did he said something came up with his sister (in Brooklyn), and he apologized but said he had to cancel. I asked him if everything was ok and if there was anything I can do, and he said it was a long story, thanked me for offering help, and said he’d reach out later. I didn’t hear from him the rest of the day Sunday or at all on Monday, so Monday evening I sent him a text just asking how he was doing. It’s now Tuesday evening and he still hasn’t responded. I’m confused because nothing ever gave me the impression that I wouldn’t see him again, but obviously I know its not a good sign that I haven’t heard anything. Do I just leave it be and wait for him to reach out again, if ever? Or is it ok to give it one more shot in a couple of days to see if something is seriously wrong?

    • Hey Suzanne – I know how disappointing this is. But I don’t see a reason to text again when he hasn’t responded to your first two texts. Let it be. He knows how to get in touch. Women often worry there is something wrong but usually its nothing but a change of heart. If it turns out there is something serious with his sister, he’ll tell you when he’s ready. But if you continue to text and there is a problem – he’ll feel pressured.

      The only way to win here is to let go and realize you may need to move on. The hardest part about dating is you don’t get any explanation as to what caused a change of heart and there’s absolutely nothing you can do about that but accept it. I know it stinks but that’s the truth.

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