Proceed in this relationship is you can: Put yourself second to the kids a lot of the time-- because they are going to need him at times you want to be with him, but he can't cut himself in two. Be prepared to have some interaction with his ex. That can be difficult if the ex is a real piece of work, and resents you in her ex-husband's life. Hopefully not, but it's not uncommon. See him only when he doesn't have the kids with him if you want the attention on you, because once three kids enter the picture, it's unlikely you'll get much of it. If he's got the kids, and something comes up at work, be ready for him to ask you to babysit. Some kids are fun, and accepting of others  -- yet some are a complete pain in the butt; especially if their mom isn't around and they start comparing you to her -- or they won't take orders from you because "You're not my mom!"  His finances may be stretched thin, so plan on limited outings that cost money if this is the case. These are some of the things that come to mind when I think of what could make this relationship -- with this good looking, smart, ambitious guy -- go sour. Now, if you are an easy going girl who loves kids and is completely flexible -- that's a plus. If you like picnics on the beach with the kids and don't mind sand in your food because you think "Gee, aren't they cute?" or "No problem, I didn't need to finish that sandwich" then, that too, is a positive sign things could work out for you and him. If you can sit back and watch Dad discipline the kids without you feeling the need to chime in, better yet. And if the relationship really gets going, and you want him to make a commitment to you, be prepared to make your life instantly filled with one big happy family -- his kids -- maybe his ex and her family -- and any children you may have together. It would be a big tent, require a lot of patience, and a belief in "more is better." Did I miss anything?