Dating a Woman with a Son

Being his Mom's boyfriend does not in any way mean he must like you.

And vice versa.

I dunno bout that. If you can't find some way of liking a man or woman's kids, I can't see how a relationship would work.

These days many men from their early 20s and older may find themselves dating a woman who has a son from a previous marriage... often a boy from about five to 10 years old. Having a relationship with his Mom means having a relationship with him too and that can be terribly tricky... especially since HE sure didn't ask for this new relationship. It's a great idea to give more than passing thought to how to proceed. I've done this multiple times with good success and, in fact, some of those boys are now young men and still my friends. So I'm going to offer some unsolicited food for thought.

Think about the position the boy finds himself in when his Dad is gone and Mom starts dating. Likely he still loves (and misses) his Dad and is loyal to him. Very likely he has anxiety because in his child's mind it is possible his Dad may doubt his love and loyalty. He also now lives where there is no big male protector and example, and he knows that he, himself, is a poor substitute for a grown man as a protector and he is also acutely aware of having lost his closest, most trusted example of "maleness". This is all his new, unasked for, home environment. And it is the situation where you show up. YOU are - to the boy - a big, strange man entering (invading) his (formerly) safe territory (home). YOU show up out of Nowhere with some strange power re: his Mom (who is all the protection he has at home). YOU are obviously some type of "challenge" to the Dad he loves and misses and wishes to God was there right now. And his Mom is telling him he has to be nice to you even though he doesn't know how you are going to treat him. You might be mean to him because he is his Dad's son, not yours! His own Dad may get mad at him for allowing you in the house! He is in a heck of situation for a young boy.

First tip - make absolutely sure the first few times the boy meets you are NOT at his home (his "safe zone") so he does not have to begin the relationship by perceiving you as a major threat. That way he still has his "safe zone" to retreat to.

Be prepared for him to talk about his Dad and things they did together. Respond with approval so he understands that you don't consider his Dad an "enemy" or "bad", and thus you don't consider HIM an adversary or "bad". Even if there IS "bad" to say about his Dad - don't you say it.
Don't ever try to "replace" his Dad or "compete" with his Dad - in any way. Let him have two grown male friends - his Dad and his Mom's boyfriend. He will understand they are different. Make sure he knows YOU EXPECT him to love his Dad as much as he can, and that you are pleased if he will like you too. NEVER question or criticize his liking or loyalty to his Dad.

Being his Mom's boyfriend does not in any way mean he must like you. You don't have to spoil him or "buy" him, but you do have to treat him with a fairness that allows his Dignity to remain in tact. Leave all discipline to his Mom and do NOT let her try to shove it off on you. Have that talk with her early on. If his Mom disciplines him, make sure she knows NOT to do it in front of you because that would be a double blow to his Dignity.
Those embarrassing episodes are strictly between he and his Mom.

Congratulate him when he does something he's proud of. Laugh with him when there is something silly going down. Help him tease his Mom once in a while. Let him beat you at "Checkers" 500-6-- times. Listen to him when he speaks to you. Reassure him if he's bugged about something but let him bring those things to you in his own time and way. Be good to his dog. Don't tell him how to act - show him. Look him in the eyes, and smile.

Obviously there is a lot more to it and kids come in a million different types and attitudes. But for every one of them you have to have the Basics in order and the things above are things I've found that have helped a lot. (Actually a lot of this will apply to a child of either gender).

Local opinion(s) may vary.

GR8...

you wrote...

"I hope that someone in their early 20s does not have a child that is 5 years old, and certainly not one that may be 10 years old. A guy in his early 20s could well be dating a 29-yr-old woman who had a 5 or 10 yo child.

If a child does not like me or I don't like the child then that is a deal breaker for me and it should also be a deal breaker for the child's mother. As indicated twice - I was addressing the child's point of view - not the man's or the mother's.

Why would all of this not also apply to dating a woman with a daughter? Well look at the last sentence which does address child gender.
Or for that matter a woman dating a man with a child of either sex?
That does happen to be a different situation, one not addressed by me and I did not delegate to you the duty to demand that my post be All-Inclusive nor did I invite all the "Semantic Correctness" (kin to Political Correctness among other rude ignorance.). But you are certainly very, very welcome to take a break from sniping at the posts of others and intitiate your very own post(s) tailored 110% to your liking whenever the mood strikes you. In fact, FWIW, I encourage it.