The other day I published a long article about my pickup history and how my interactions with women changed from my 20s to 30s. In my case, it is also important to add that I am older than I look. Even in my mid-30s, women thought I was in my 20s. Of course, time will grind all of us down eventually and no matter if you look your age or not, at some point you will no longer look young. This will drastically change how women interact with you. As I sidestepped this issue due to good genetics, the following is based on observations as well as conversations with friends but also interactions with real-world coaching clients in the past. Most guys who paid me for coaching them in-person were older. In fact, the specific problems they were facing as somewhat older guys where often the reason they reached out to me.
Before we start, I want to exclude the case of older women. I assume that even in your late 30s and beyond, you would much rather pull women who can bear children without the need for expensive medical treatments with low success rates. Older women tend to be quite desperate. They are the easiest to pull for a one-night stand, and they almost beg guys to enter a relationship with them. Regarding young women, the biggest hurdle you face as an older guy, assuming that you are in decent enough physical shape, is that women will distrust you, and rightly so. The first question on her mind will be why you are not in a relationship or married already. She will be curious about how you spent the last twenty years or, more generally, how you ended up in the position you are in. Do you have a good answer to this? I am not saying that there are no good answers, but you should be prepared for this.
When you are in your 20s and some club slut you pulled for a one-night stand asks you why you are single, you can plausibly say that you just have not found the right one yet. This will resonate with her because she likewise has not found the right one yet (and probably will not find him ever). Yet, why would you not have found a girl to settle down with as a 35 or 40 year old guy who has so much going for him? Thus, she may assume that there is something you are hiding. In fact, some women make the default assumption that any older Chad who rails them is cheating on his wife. Their default assumption is that you are married or perhaps even have kids and thus she is just auditioning for the role of being a side piece.
There are some plausible explanations for not having found the right woman yet but telling her that all women are whores, which is why you don’t want to ever settle down is none of them. Moving across countries could work. Building a now successful business is a great explanation. Telling her that you have come out of a bad relationship is probably not a good move as it signals that you did not do a good job picking a partner. Again, this is fine when you are 25 but if she hears this out of the mouth of a guy who is 45, she will likely picture you going from one bad relationship to another.
A very plausible reason for you looking for a new woman as a somewhat older guy is of course that you divorced your ex-wife. This is quite a problem, though, because this implies that you may have to pay alimony and possibly child support, too. Only really well off guys can shoulder such fiscal demands easily. I know a few guys who are still in good enough shape to get young women based on looks but as soon as those women learn about this, they lose interest fast. Sure, she may stick around to bang you a few more times, but this is a game you cannot play so easily. Even if you are in stellar shape (for your age), guys fifteen years younger who are in stellar shape for their age will play in a different league. If she can get those guys, she will jump ship. In my case, I think I would have been screwed had I to pay alimony and child support to my ex-wife — we did not have children and got out of alimony payments due to a prenup.
Lastly, if you really want to settle down, I think you should not put this question off for too long. In your late 30s or early 40s it is about high time you sort this out. Of course there are good reasons why you are older, reasonably successful, and single. If you are perfectly fine with this kind of lifestyle, then more power to you. However, the fun single-guy lifestyle has an expiry date as people half your age will normally not want to hang out with you, and vice versa. Peers your age normally also have a different lifestyle, so it can feel quite lonely to be an older trying to extend his adolescence for a few years. I have heard remarks to this effect from a surprising number of people, and this includes guys who have really made it, like a former client of mine how has an eight-figure net worth or a good friend of mine who sits on about two million euros and does not even have to work anymore.