What Would Debbie Do

What Would Debbie Do? Dear Debbie, I’ve been dating a guy for about two months and I really like him. He seems to really like me too, but I find he’s constantly holding back when it comes to candid discussions about his dating past. I feel like he’s hiding something. Is it right to press [...]

What Would Debbie Do?

Dear Debbie,

I’ve been dating a guy for about two months and I really like him. He seems to really like me too, but I find he’s constantly holding back when it comes to candid discussions about his dating past. I feel like he’s hiding something. Is it right to press him on this?

                          – Janet

Dear Janet,

As women, I think we love to know the salacious details of a man’s past. Unfortunately, it usually creates more anxiety than we’re prepared to handle. You might think you want to know what his girlfriend looked like, how sexy she was, what they did in bed, whether or not he loved her or any other juicy tidbit you can think of. But really, this information will create some type of benchmark that you think you need to meet and surpass. And then if you don’t, you always wonder if he still thinks of her, or wants her. When you think about it, this is nutty!!

Living with a ghost is impossible, so just be your self. The past usually comes out with time anyway–through his actions, his comments and the way he treats you. Plus, two months is way too early for a guy to begin spilling his innermost secrets. I say chill out and let the relationship evolve with time. Telling your “sad stories” about lost loves and wounded relationships is a killer for anything new. Leave it alone.


Dear Debbie,

I’ve been on three dates with a guy I met at work and he keeps taking me to really fancy restaurants, which of course I love. On the first two dates I did the “obligatory reach for my wallet”, but he insisted on paying. On the third date, he let me know exactly how much I owed, down to the penny. Even afterward when we went for drinks, he divvied up the check down to the very last beer. I don’t know what happened—did I ruin it by reaching for my wallet? I know for a fact that he makes a lot more money than I do, shouldn’t he pay? After all, he’s the one who keeps inviting me to swanky places.

                          – Broke in Baltimore

Dear Broke in Baltimore,

This one really bugs me. OK, OK, I’m a traditional girl. Boy asks girl out, boy pays for girl. PARTICULARLY if boy takes girl to expensive restaurant! I probably would have slapped you for reaching for your wallet in the first place, but hey, that’s my thinking. If a guy wants to ask me out, he better be prepared to pay. You have to decide whether or not you want to stand behind my personal philosophy to begin with, or you’ll find yourself exactly in the place you’re in right now with the next guy. You did reach for your wallet, my dear…now he thinks it’s OK. So what is it? You think it’s OK to pay, or you don’t? You offered, but now you’re resentful or annoyed, even touting his financial prowess. Set the record straight right now. Either you will or will not pay. If he balks, you might need to find yourself a new guy or risk being annoyed continually, which will only create contempt in the long run. I say next time leave your wallet in your purse right from the get-go.


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