Leave one in place and slowly slide your hand down her arms and over the back of her hand. Does she smile at you and hug you? Try and keep the humor relative to the girl. Yes, you will feel cheesy, and he might think so too, but if he's hot... You're going chicago chat rooms out to enjoy yourself, after all. You can ask about her kids, but it is better if you don't. Decide which one of the options would make you a better person. Unfortunately, that's likely never going to happen. She might not just like you as something more than a friend. This is the most important step. It's no use playing 'cute' because your boyfriend won't be able to see the true you. If he has, you two can talk about what you think. If you persistently demand a precise combination of attributes up front, you'll probably fail to find it, maybe even drive off someone you would like with your fussiness, and finally, jaded, settle for a relationship not off to a good start for either of you and perhaps awkwardly late for a family. Are they moody or do they hide things from you that you should reasonably expect to know?