Ben Claassen III (For Express)

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Q. I am dating someone well-known in our community (think respected blogger in a certain field). I am really into him, but I also feel that I don’t have a sense of being on a level playing field with him. I had gotten used to feeling pretty accomplished, at least on par with who I date, and I tend to feel like I’m the attractive one in a relationship. Now I feel like I’m the appendage. He’s not famous-famous, but I feel eclipsed in his circles. I don’t like what this says about me, though, and I’m wondering if it will get better with time. Is there a way to get over this? Or do I need to be the star in the relationship? —Uncomfortable

You’re dating someone with whom there is a new dynamic and balance of power and status, and that may take some adjustment. It doesn’t necessarily mean anything negative about you. After all, a history of always feeling like the attractive one in your relationships could mean many things — from being smokin’ hot while not needing partners to be that way (great!), or pathologically needing your partners to feel grateful just for getting to hold your hand in public (not so great). There’s no way for me to know here, but I’ll err on the side of not pathologizing: You’re human, your partner is not the typical partner, and so your reaction is natural and understandable. Give it time and see where it goes. You’ve said nothing about what this guy is actually like and whether you like that — regardless of his fawning admirers. Ultimately, you choose to be with the person, not the image. And the positives will either overrule the negatives or they won’t.

We used to do it. Do I tell her?

Q. I have some history with a guy my friend is now dating. Nothing serious, just a few hookups when we knew each other years ago. She knew that we were acquaintances, but she has no idea otherwise. I keep going back and forth on whether to say something to her. For what it’s worth, they don’t seem serious yet. My gut says to let it go, but I also feel like if it does come out someday and I never said anything, then that will be a bad situation. —Torn

There are two truths here, and they’re at odds. One: For sure, it is far better for her to find out now than to find out later. Two: On any given day, it is easier if she doesn’t find out at all. But, easy doesn’t necessarily mean right. I’m not sure how close you are to this friend. Is it fair to her to withhold this? And imagine having to sit on this secret potentially indefinitely — or even worse, wondering if others who knew of it, including him, are going to spill the beans regardless of your wishes. It definitely runs the risk of becoming A Thing. I’m generally in favor of preventing the growth of such Things. And if they are not yet serious, hopefully this should not (yet) be a humongous deal.

Send your questions for Baggage Check to Dr. Andrea Bonior at She may answer them in an upcoming column in Express or in a live chat on Tuesdays at 1 p.m. at

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