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Hey, it’s Mike Fiore with your weekly Digital Romance Newsletter. This week, we’re going to talk about dating when you’re older, and the problems with “text dating”…

But first!

Thanks for all of the responses last week on our email about p@rn. We love hearing feedback! Start up a conversation with us by sending your thoughts to

Mary asks,

I am a healthy, happy, single, young at heart 55 year old woman. A guy I know from high school, messaged me and confessed he always had the hots for me in high school. That was actually like a year ago. Recently, he asked for my phone number, as he was getting off of FB, but, would still like to stay in touch. Long story short, we have been texting for a good month, and we have confided in each other our deepest, darkest secrets, as well as several of our sexual fantasies. He lives over 1000 miles away, but, I expressed interest in a relationship with him. My kids are grown and I am willing to move eventually. We think about each other CONSTANTLY. He tells me he’s not ready for a relationship, but, maybe in 6 months or a year. I am on a dating site and just can’t think about anyone but him. Should I just push him to the back of my mind and move on?? I just don’t know what the hell to do. I texted him the other day and simply said…. ” just wanted you to know I was thinking about you, even though I don’t want to.” He responded with…. “Would it surprise you to know that when you tell me things like that it gives me an instant hard on for you?”….. I know you’re crazy busy with emails, but, please…. HELP A MOTHER OUT HERE!!!!!! Lmao….. Sincerely, Mary

Hey Mary,

First, let’s dive into dating when you’re older.

Looking for Love? When Is the Right Time!Dating later in life, or after a long relationship is freaking hard, and you should give yourself a bit of a break. I mean, after years (or decades) of being in a relationship (and often feeling like you’ll never need to “date” again) jumping back into the world of singledom can feel a little like having to repeat all the uncomfortable parts of High School again.

One of the absolute BIGGEST mistakes I see folks make after the end of a marriage or a long-term relationship is immediately DIVING in to a new one with the first “Pretty awesome” man or woman who comes their way.

(Men are actually way worse about this than women are, by the way. Older guys get so used to having a woman around to “take care of them” that they often seem absolutely helpless when single.)

Anyway, I guess what I’m trying to say is “I get it” and it’s 100% normal for you to feel a bit lost and nervous about dating again.

You were married for 20 years or you were dating for 8 years etc. etc. and being IN relationship is what feels comfortable. It makes total sense that you’d want to jump at the chance (sometimes without even realizing it) to be connected again (especially with a guy you can give a hard-on with a simple text message.)

But I want you to slow down a bit.


Because, plain and simple, you aren’t READY for another relationship yet.

You haven’t given yourself time to heal, reflect and learn about yourself.

See, when you get out of a long relationship the most important thing for you to do is take the time to discover who you are again.

“But Mike, I KNOW who I am!,” you might whisper-scream into your computer while reading this newsletter.

But No.

You really don’t.

You know the Mary who has been in that long term relationship really well.

But you don’t know Single Mary at all. And you need to take the time to figure out exactly who Single Mary actually is.

What does Single Mary like to do for fun? Who are Single Mary’s good friends? What does Single Mary want to do on a Friday night? (Not what compromise is Single Mary willing to make to make her partner happy, but what do YOU actually want to do.)

I’ve said it before and I’ll say it again: when you get out of a long term relationship, you should go play the field. Play the field with yourself and with others.

What I mean by that is take yourself on dates. Go on dates with others. Take yourself to an event YOU want to go to. Find someone you are interested in and go to an event with them. It’s just as important to focus on you as it is finding another partner.

Honestly, I would recommend you stay single for 6 months. This isn’t a one weekend exploration of yourself. You need to create habits, break habits, make discoveries, make routines etc.

Because once you take the time to focus on single you, and explore single you sexually and non sexually, you will have a much better time at finding love.


Mary, you said you’re single and since you have kids, I am assuming you were at one point in a long term relationship. So, before we get any further, make sure you are taking the time, or have taken the time, to be single you.

Let’s get back to our mystery man…

Red Flag #1

The line “I’ve had the hots for you since high school” makes me want to barf up my oatmeal from breakfast. It’s the same as those horrible pick up lines we all know:

Did it hurt when you fell from heaven? Cause you must be an angel.


That outfit is very coming on you. Of course I’d be coming on you too.


Do you have a breath mint? I just threw up (I have actually seen this one in action. It worked, he took her home and they hooked up…I know right?)

Seriously. Could he be less creative? Even if he did have the hots for you in high school, he’s saying he thought teenage you was hot enough to think fondly on when he’s alone. (Maybe that’s a bit far, but you get my point).

Red Flag #2

He’s getting off FB so can he have your number so you stay in touch? I’m gonna be honest here, how many people do you actually know who have “gotten off FB” and never come back? I’m sure there are some, but it was a sleazy way to get your phone number rather than just saying “Hey, I like you. I’d like to connect further with you. Can I text you?” or “I am really enjoying talking with you and I’d like to text you or call you. Is that okay?”

Red Flag #3

He lives of 1000 miles away…

I think this one speaks for itself, but just in case…

If he lives that far away he could be doing anything. You haven’t seen this guy in years. He could be married. He could be a silver fox. He could have warts on his nose. Being that far way ensures that you two will probably never see each other and might be the reason he reached out to you (ouch).

Red Flag #4

He said he isn’t ready for a relationship but might be in 6 months or a year.

What the hell does that mean?

Is there a magic wand that will be waived in 6 months to a year and he will magically be ready to date you?


It means he’s NEVER going to date you. He was NEVER interested in dating you. He is flat out just having fun for himself.

And this leads us to our bigger problem

Texting is fun. Texting can be sexy. It’s so easy to spill your soul to a little white screen and cursor because you aren’t face to face. There is something in between the two of you. It makes your confessions almost innocent. For some reason we all feel that we can say ANYTHING to that little cursor and whoever is on the other side because we aren’t face to face.

The problem there is that it also means your relationship isn’t real.

You’re having a relationship with your phone.

The reason you can’t think of dating anyone else is because you are having a relationship with your phone and it’s fun and safe. It’s easy to say dirty things or share secrets to that screen but it pales in comparison to finding someone you can share those with face to face. That’s the real deal.

Listen, lots of relationships start with chatting on a phone or website or email but you have to GET TOGETHER IN PERSON. You’re never going to know if something is real or if something is possible if your entire relationship is through a device.

I actually give this exact advice in my Online Allure Formula program for online dating. If you start talking with someone meet up with them within 2 weeks. If they aren’t willing, walk away.

So, Mary, what should you do?

Tell him thanks, but no thanks.

“This has been fun but it’s not going anywhere and isn’t going to go anywhere. Thanks for the chats, but this is over”

DON’T respond to begging, pleading, or threats. Just move on.

Some of you might be thinking “But what if he’s the one!? What if I wait those 6 months and he does want to date me and we end up happily ever after?!”

Nope. Sorry. It’s not going to happen.


Plus, what are you going to do for those 6 months? Sit around and ignore all the other men you might have a chance with? What if you miss out on THAT great love? See, it’s a vicious cycle.

Know your ground rules, stick to your ground rules and make sure, above all, you value yourself and your time.

Phew! Thanks guys! Agree? Disagree? Let me know at



P.S. Want to learn the secrets to online dating? Want to have men asking you out every day? Go check out my Online Allure Formula now and change your dating game forever.

Michael Fiore

Internationally recognized as the foremost expert on how to have great relationships in the modern world, Michael is blunt, funny, and always honest.

In 2011, Michael appeared on “The Rachael Ray” show with his popular “Text The Romance Back Program” (Rachael said he gave her “chills”). Since then Michael has given women X-Ray vision into men’s minds with “The Secret Survey”, helped thousands rebuild relationships with “Text Your Ex Back”, and has become an Amazon Best Selling Author.

Michael lives in Seattle, WA and is currently hard at work on his next shocking, straightforward and really, really useful program.

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