Be Careful How You Unload Your Baggage

Men's Dating

Be Careful How You Unload Your Baggage

Nick Slade Nick Slade • 9/25/14

She knows you weren’t born yesterday. She loves that you are a man of ample experience in business, sports, music, cooking — whatever your expertise may be. And she is willing to accept you come with a romantic history and baggage, just as she does. But there’s a time and a place to fill her in on the details. If your timing is bad when you bring up the ex, she might just bring down the ax.

Honesty and a willingness to be forthcoming have to be balanced with common sense and the need to get your new relationship on solid ground before you test her fragile new commitment to you. The key is threefold: don’t tell her every time something reminds you of your ex, especially in a fond reminiscence; keep the discussion about the exes away from your romantic candlelit times together; and put the discussion into a controlled, comfortable and casual setting.

So, you’ve had a few great chats over coffee and some all-night phone conversations, and now you’re on your first dinner date when she asks you about your ex. You’re not in the mood for that, so you deflect the question. But she keeps coming back to it. What now? You can’t lie, and you can’t just keep blowing off her question.

You reach across the table, clasp her hands firmly and look her in the eye. Your smile relaxes and charms her, but you can see she’s feeling a bit emotional and wonders if you have something to hide.


“There’s no point in telling all right

away, in case things never take off.”

Remind her tonight is about you two by saying something like, “Baby, I am going to tell you everything there is to know about me, but I just want tonight to be all about you, all about us and our new beginning.” Then mock her a little: “My ex and I don’t have a love child. She has no restraining orders against me. She isn’t a crazed killer obsessed with my new girlfriends. It was just a relationship that stopped being good.”

You can see your new lady is a little more relaxed, but you’re only halfway home. You have to let her know when and where this will be all be reconciled. Try saying, “I want to start at the beginning and tell you the whole story because if our relationship keeps getting better, as I think it will, then you deserve to know everything. Come over to my place on Saturday, and you can ask me anything you want for an hour or as long as you want.”

If you do have something major to disclose, like a child or a previous marriage, you should drop a few hints that you want to tell her your story sometime. There’s no point in telling all right away in case things never take off, but you can’t wait so long that it seems like you were hiding a bombshell when it finally comes out. When things start getting just a little bit serious, schedule a talk with her. If she’s the one for you, she will understand and be supportive.

Oh, and when she asks, “Were you in love with her?” it might be best if you go with something like, “I thought I was at the time, but now it’s only you I’m crazy about!”