Reading Time – 3 minutes

What I’m about to describe has always been a problem with men in my experience of talking to thousands of them over the past almost 20 years about their dating and relationship lives.

But for some reason, not only has this problem not improved, but I see it getting worse.

The problem is this:

Too many men between the ages of 30 and 45 still have no idea what they want in terms of their long-term woman lives.

I will talk to men between the ages of 30 and 45 and ask them questions like:

Do you ever want to get married (OLTR version of course)?

Do you want kids?

If you want kids, how many? When do you want them?

Do you want to settle down, or not?

Do you want a long-term girlfriend or wife? Or not?

If you do, what would that relationship ideally look like for you?

And way too often, I just get a blank stare as an answer. Or a nervous hesitation. Or a wistful look up at the ceiling.

Or an answer like, “Uhhh… well….uhhh….”

Or just, “I’m really not sure.”

If you’re in your twenties and you don’t know what you want for your future in terms of your relationship life, that’s fine. Frankly, a lot of guys in their twenties have the opposite problem; they want a girlfriend or wife when they shouldn’t have anything like that yet.

If you’re in your early thirties and you still don’t know, that’s okay, but you should at least start thinking about it.

But holy shit, if you’re over the age of 35, and certainly if you’re in your forties already, and you still have no damn idea what you want in terms of your long-term future concerning relationships with women, kids, settling down, and so on, this is a very serious problem.

If you never want to move in with a woman and/or never want kids, that’s fine, but you should know.

If you want to get an OLTR at some point, that’s fine, but you should know.

Not only if you want these things, but also a good idea of when you want these things.

If you are over 35 and don’t solidly know what you want for your future in these areas, here’s what’s going to happen:

1. You’re going to spend the next 10-20+ years of your life floundering around with a bunch of half-assed relationships that don’t work. Having that problem in your twenties or thirties is one thing, but do you really want to fucking around with that garbage in your forties, fifties and sixties?

2. You’re going to start feeling like there’s something wrong with you (and you’re partially right!)

3. Worst case, you’re going to either get a woman pregnant by accident and just go along with a situation you didn’t plan (nightmare) or you’ll eventually succumb to oneitis and just marry/settle down/get monogamous/some other stupid shit just because some woman you’re dating stamps her little foot and makes demands (nightmare, and divorce/breakup city).

I’ve seen these things happen over and over again with middle-aged/older guys, and it almost always traces back to the fact that they don’t know what the hell they want.

After my divorce, way back when I was 35, I knew exactly what I wanted for my long-term future with women.

I told myself that eventually I wanted to settle down with a new woman in a non-monogamous marriage-type relationship with many FBs on the side (I didn’t have the term OLTR back then but I still knew it’s what I wanted), that I didn’t want any more kids (because I already had two), but that there was no rush for me to settle down again and that I should wait at least 10-15 years before doing so, and in that 10-15 year interim period I should go have sex with a bunch of hot FBs and MLTRs and enjoy myself.

And that’s precisely what I ended up doing. Because I knew what I wanted.

If you are over the age of 35 and you still don’t know if you want to settle down or not, if you want kids or not, what your ideal perfect long-term relationship with a woman would look like, then for fuck’s sake, you need to figure this out.

Throwing your arms in the air and saying, “But Caleb, I HAVE thought about it and I just don’t know!” isn’t going to cut it. Not for an older man like you. (Younger guys are allowed to not know what they want; you don’t have that luxury.)

Sit down with a notepad or blank document and just think it through. What do you want? What do you not want? What do you THINK would make you happy in your fifties and beyond? What do YOU want (not what your mom or girlfriend wants)? And so on.

Just write things down and brainstorm. Then do it again a few days/weeks later. Then do it again.

Figure this out.

You’re playing with fire if you don’t.