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If you’re very young, it might come as more of a surprise to your date than if you’re a bit more mature, so you might want to make a special daytime date to tell him your story. This way, he’ll know something’s coming, so he will be prepared.
If you’re a bit older, most guys aren’t going to mind if you have a child or two. If you have a brood of seven, it could be a challenge.
The key is not to hide it and not to wait too long. If you had to go through hell and high water to find a sitter three weekends in a row for hiking, rock climbing and jet skiing, he’s not going to expect that you are usually tied down with family obligations. Tell him before the second big adventure, or it may seem like you were being dishonest in the way you portrayed yourself.
If you’re being intimate with a man, he will often be able to detect the tell-tale signs of motherhood: that little indentation above your belly button, those small white stretch marks on your tummy or breasts, tummy skin that is just a little bit looser than the rest — which he can even notice in the dark.
Don’t wait until he’s pulling your sweater over your head before you tell him. A child is an important part of your life, so you want a man that will accept all of you. If it doesn’t come up in conversation by the third date, you either aren’t doing much in-depth talking, or you are withholding information.
One more thing… don’t wait until the “first sex” date to tell him about the kids. He will keep the date going for the sex, but if he doesn’t want a woman with children, he won’t be back. Tell him on the date before you have sex to see if he comes back for you, kids and all. If a guy is going to dump you for having kids, it’s better to find out sooner rather than later.