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Ask Ann Cannon: My boyfriend wants to spend Thanksgiving with my family, but I’m not ready

Dear Ann Cannon • I have been in a serious, exclusive relationship with a man for the past six months and I’m happy to say things are going very well. For the most part. We have recently come across a conflict on a specific situation.

Some backstory: I tied the knot at a young age with my college (and first) boyfriend. We were together for years, but as it sometimes happens, we grew apart and decided we were better as friends rather than as a family unit. There are no kids in the picture, which has made entering a new relationship easier than I imagine it might have been otherwise.

The person I am currently seeing is only the third romantic relationship I have ever had up to the age of 36. The conflict for which I am seeking advice is as follows: My boyfriend is very enthusiastic about meeting my family and getting involved in that part of my life. He would very much like to come to my family’s Thanksgiving dinner. I am hesitant to do so at this point, with my decision being based on various complicated dynamics that define my large family. I have several siblings, all of whom are married and all have two to five children; my parents have been married for 43 years, and while we are close and genuinely get along with and support one another, I have made life decisions that differ from those of the rest of the group, which is slightly alienating. Subsequently, my family views me and my life through a slightly different lens than that with which they view each other, whether subconsciously or not. Due to all of these factors and the intricate subtleties at play, I am not ready to start bringing my current boyfriend to family events, especially one as big as Thanksgiving. The only person I have ever brought around was my former husband.

While it pleases me that he wants to know my family, and thus get to know me better, I simply don’t feel ready. The problem is, no matter how in-depth an explanation I give him to explain my hesitation, his feelings are hurt, and I think deep down he worries that I am ashamed of him or I don’t believe our relationship will last. While I’m not able to make any solid statement on how things will turn out for us, I feel very solid about our connection, feel genuinely close to him, and am definitely NOT embarrassed by him, nor am I ashamed of anything to do with him. I am simply not ready for the integration of this relationship with my family. The last thing I want to do is make him doubt his value or the solidity of what we have; that being said, I am not going to concede and have him accompany me to a holiday dinner.

Because I am unwilling to bend and have explained in depth my reasons for waiting to have him come around, he is feeling unintended but very real hurt. I don’t know where to go from here. Any guidance on how to navigate this one?

Cautious to Consolidate

Dear Cautious • I do understand your reluctance to invite your boyfriend over for Thanksgiving dinner. Large family holiday gatherings, even under the best of circumstances, can be … fraught. I also understand why your boyfriend feels hurt. And, frankly, it doesn’t sound like there’s much you can do to fix that, short of changing your mind. I’m sorry.

Meanwhile, do you foresee a time when you’ll want to introduce your boyfriend to your family? If so, think about having him meet your parents and your siblings on a one-to-one basis instead of as a group, thus allowing everyone involved to sidestep problematic group dynamics.

Speaking of which … is it possible that you’re making assumptions about your family members’ attitudes toward you because you’ve chosen a different path? Is it also possible that they actually care less about your choices (especially if time has passed) than you think they do? Just wondering. It’s very human, after all, to project our own insecurities onto the people around us.

I sincerely hope things continue to go well for you and your boyfriend. Best of luck!