Should I stay or should I go? (date or not to date)

As a stranger to you on the Internet, it’s hard to say. All I can think of are questions to ask you:

How old are you? If you’re 20 and he’s 27, that’s a vast difference. However, if you’re 30 and he’s 37, the difference doesn’t seem so severe.

I’m curious why you’re worried about his divorce. Will it affect a relationship you might have with him? That relationship is past. I suggest you concentrate on the present.

I have questions about him:

Do his children live with him? That is a very important piece of information. If they do, then you are right to be highly concerned about them and any relationship you may have with them and their father. If not, why worry?

Has he said why he wants to meet you? Is there something he wishes to learn in person that he can’t learn otherwise?

All in all, there are too many unanswered considerations for me to advise you.

I would say date him. How many people in their life time across the world come across this sort of opportunity to gain this sort of experience? In the end, I think you’ll learn a lot about yourself anyhow. Which is always a positive in my book.

Hey Hawaii Jake,
I’m 24 & He’s 31. I think its more of the “he already has kids” aspect. He seems to get on well with his ex & his children arn’t as young as I thought (8 & 12).
His kids don’t live with him, he says he sees them as mush as he can (he could proberly see them more). He said they mean everything to him & that hes careful about the woman he talks to which is understandable because of the kids.
He seems to like me in general, he said the more he talks to me the more interested he is & that he would be happy if a relationship between him & I happened down the line.

@silvermoon, all that sounds quite positive actually. I would say try a simple date and see what comes up. Meet him at the coffee shop where there will be other people around.

It’s good that he sees his children as much as possible and that he’s careful in considering what kind of woman he might introduce to them. That shows he’s considerate and caring and even loving.

I say go for it, have fun, but don’t expect too much.

Perhaps you want us to throw around Pro’s and Con’s? There is an age gap, not serious. These days all different ages are getting together, and in the end its the person that counts. How they treat you, how they make you feel. How they relate to the world, what their perspective on life is. How they see their family, and treat them. Whether they are honest, can be trusted, can communicate, can bridge gaps. Children are a responsibility whether they live at his home or not, they require monetary care, emotional care and are human beings too of course. I think any “obstacle” can be beaten if the parties involved care and can discuss things.

I just found out that hes not 31, he is infact 38. He did a typo and he for some reason thought that I was 30!

I don’t think it sounds like a good fit.

Are you prepared to be a stepmother to an 8— and 12-year-old?

Are you prepared to be tied down with a guy 14 years your senior?

I don’t think you should let this go any farther.

I also don’t think the Internet is the place to find guys.

So let’s see..you’re closer in age to his oldest child than him (just 12 years apart from his 12 year old and 14 years apart from his)...
He’s on the edge of GenX and graduated in the early nineties..which is a different set of movies, music and cultural cues than the ones you grew up with..

Does this doom your relationship from the get-go? No, not necessarily.. but answer this:
If his kids are that old and he’s pushing 40 do you really think he wants to re-marry and start a second family? Are you interested in never having a child of your own?

You may be thinking: “Uh, I only wanted to know if it was worthwhile to date the guy—not planning a family today, thank you!”...but really, why start dating and potentially fall in love and get entangled with a man and his kids if the end result is that you couldn’t see yourself married/together long term.

Most guys I know in his age range (which, btw – is about my same age, and my kids are his age…so I know quite a few 38 to 45 yr. old guys) are NOT interested in starting over and having a 2nd family or another baby. You get to the stage where your kids are getting pretty independent and fun to hang around with and you cannot imagine going back to diapers and strollers and sleepless nights with an infant.

Also, considering it’s the internet..he could be entirely misrepresenting his marital status and how well he and his wife/ex-wife get along…

Most guys I know his age and even into their 50s who start over also seem to start new families. I’m not sure who @geeky_mama knows, but I find her statement very surprising. Guys love to have more kids. Especially with a younger woman—because she can keep up with the kids and he gets to do the more sedentary stuff. Although they also like kids because they keep a man young.

At best, this is probably something no one should generalize about. It’s an issue. Does he want more kids? Would he have more? Too soon to ask. But something to think about.

The age gap is not a big deal, unless you have prejudices about that as many do. But many young women like older men. They are more stable and more mature and know more about what they are doing. Young women with “daddy” issues are often attracted to older men. They are looking for security they may not have had growing up. These are not bad things.

Older men like younger women because they are younger and sexier and better equipped to have kids. Also they may be more pliable and agreeable than older women, who know their minds better and have more confidence. Older women would say older men who like younger women are immature. I say, so what? But that’s theoretical, since I’ve never been in a real life relationship with a younger woman.

If the relationship lasts, then you can pretty much count on being relatively young when he dies. Issues of being involved with his children are problematic. It is not easy being a step mother. Few step mothers are able to treat step children equally with their own children. You probably shouldn’t even try. They are his children. Sometimes they are roommates. You want mutual respect, if possible. You can’t order them around.

The psychological issues of why you would be attracted to an older man are something to investigate, too. Therapy would be a good idea. You want to develop into a mature woman on your own, and that can be hard in a relationship with a much older man. You can get set into ways of relating that aren’t healthy over time. You may find your independence of thought being corralled. He may resist changes in the power between you over the years. Those are things I have seen. They are tough, but you can deal with them.

Should you? Depends on what you get from him, and how well you think you’ll be able to work with him. Hey! Guess what? That’s the same as it is for any relationship!

Red flags all over the place. Take it slow and find things out firsthand. You don’t have to rush into committing to anything here.

Just go, you both may not even feel anything once you meet. If you do then I would just take it slow and see where it leads. There is no rush to be intimate, or to be exclusive so you can just date each other and go from there. When its time for that discussion I would then see what your feelings are at that point. Why get so serious before you’ve even met him.

I want to know why you are questioning the date? It seems to me that maybe you are not as ready as you think you might be. When I know what I want for sure, I go for it, no questions asked. The right guy is out there, one with whom all the questions are not a worry. You’ll know it, and most important you’ll feel it. Sometimes we make mistakes, it’s how we learn. You’re whole life can’t be based on by what everyone else thinks.

If you’re questioning it this much, don’t date him. He’s almost twice your age…what could you possibly have in common?