“Help!” That’s the last line of an email we received from an anonymous user who had a serious question for us to answer. Never fear! DateSpaces is here!
The rest of the email read, “I’ve gone on a handful of dates with a guy who I think could be a potential mate down the road, but I haven’t told him yet that I have a daughter from a previous marriage. When should I tell him and how?”
This is a tough one, we know. But like many of our “Ask Our Staff” columns, this one has a similar philosophy: when dealing with relationships, the truth always needs to come out, like it or not (just ask Serena van der Woodsen from Gossip Girl how that whole “lying about her past” thing worked out and you’ll understand why). But first, Ms. Anonymous, we suggest you see where things take you in the next few dates. Maybe there are a few skeletons in his closet that he hasn’t told you. Get to know him a bit more before you drop the bombshell. Because if he is indeed “the one,” he might feel okay about helping you with your daughter some day. See how he feels about you, even though you may not be able to tell from a “handful” of dates. That said, don’t wait TOO long either. People usually want to know some of these things somewhat up front.
As for how to do it? Don’t make it a huge presentation. Sure, it’s not a casual thing to say that you come with what everyone loves to call “baggage,” but if you do it after a huge home-cooked meal and a bottle of wine (or an activity you’ve never done before), it’ll feel so much more like bribery. If it’s possible, keep it in the context of your “getting to know you” conversation. If it’s a question of your past relationships, weave it in with a “I want to tell you something about myself.” Stay confident: this is your life and your future special someone is going to have to take it along with everything else he loves about you, Anonymous. If he doesn’t want that part of it, he can’t have you and he’s not the right one.
When you do drop the bomb, send him to a few of these links: a blog about a single mom seeking, an article on dating someone with a child, and dating tips for single moms.

