I met a guy while getting my MBA about six months ago, and we have been casually talking when we see each other in class. Recently there has been some flirting going on, and we have even met up for drinks with friends a couple of times. I'm starting to have a little crush on him, but I have a child and I don't know how to tell him that. I haven't told him yet because it was always a casual conversation, but now that things are starting to take a new direction, I feel like I should. I am just really confused as to how I should tell him about my son. Any advice?
— Worried About His Reaction Reese
To see DearSugar's answer read more
Dear Worried About His Reaction Reese,
Obviously you really like this guy and don't want to scare him away, but I think the best way to tell him is just to go ahead and do it. The bigger deal that you make out of it, the more awkward it will be; he's going to take his cues from you, so if you act confident, he'll be comfortable. At the same time, don't undermine the importance of the issue. You're a mom, and that's a significant part of your life, so don't be afraid to talk about it with him. Keep in mind that no matter how you say it, it doesn't change the fact that you have a son, and in order to date you, your crush has to be OK with that — trust me on this one, if he's not OK with it, it's a dealbreaker.