I have been dating my boyfriend for about a year and a half. Things have been going well but recently he began expressing to me that he was uncomfortable about the fact that nine years ago, I used to date the brother of my now-brother-in-law (through my sister’s marriage). My boyfriend said he is uncomfortable being around him at family events. It was a serious relationship at the time — we lived together — but both of us have more than moved on since then and even hung out as friends on multiple occasions.
My sister’s husband comes from a pretty fractured family and his brother is really all he has. Also, my sister is very close with her brother-in-law.
My boyfriend has not had many relationships and I’m not sure he has had many encounters with exes. I would like to keep up our family traditions, such as Sunday family dinners, which the brother and his girlfriend of three or four years attend. He and his girlfriend don’t seem to mind about our past at all.
How do I handle this?
With a more mature boyfriend or a time machine.
You handle this by not budging, in the kindest and unbudgingest possible way.
Because you can’t budge, not without straining two families and setting a terrible precedent for ceding control of the guest list for your own life.
If nothing sketchy is going on between you and the ex, then the onus is on your boyfriend to accept that your ex has a valid place at your table. And if something sketchy is happening, then the onus is on him to break up with you, not assume control of the men you’re allowed to see.
Your boyfriend may well be new to this whole dating thing and its complexities, but that’s grounds for sympathy, not license to bust up Sunday dinner. He’s also not new to you or to this situation. What changed?
Whatever the reason: Let him know you understand it might be awkward for someone in his position, but, this is your family configuration. If he’s not comfortable with his relationship with you, then you and he need to deal with its issues on their own merits. If he is comfortable, then trusting that will help him get used to this little joke fate chose to play. As you all got used to it yourselves, remind him. Presumably there was an adjustment period at the time for everyone involved?
You adjusted, though, because it was a take-or-leave situation — accept it or excuse yourself from your family as you know it — and it is one now for your boyfriend, and will be for anyone you date as long as he is part of your sister’s life. Tell him so, take or leave, and that you’ll help him find ways to take it. Within those bounds, of course, of not budging an inch.
I have a “friend” who will email and invite me to lunch and then add, “By the way I’m cycling for charity, please contribute,” and then she never follows through regarding the lunch. Once, we actually made a date for lunch and then she said, “I’ll call you that morning and let you know if it still works for me!” and I never heard from her the day we had scheduled the lunch. I asked her and her fiancé to join my husband and me for dinner and she said, “Great idea! I’ll get back to you when things aren’t so hectic,” and 10 months went by without a word.
Although there was a time when this person and I were close and spent time together, obviously this is no longer a friendship, and I have decided not to accept this behavior from her again.
There is a strong possibility that I am going to run into her around town. What can I kindly say to let her know that I’m done with her without being snarky?
Why do you need to tell her anything? The friendship is over, there are no plans being made that you need to break, and if she ever invites you to something, then you already know she doesn’t mean it so it doesn’t matter whether you reply yes, no, maybe, or not at all.
The only thing left to do is to exist in this reality instead of the alternative one where you thought you might someday, eventually, have lunch.
If the opportunity arises naturally for you to say something, or if it’s important to you to tie off the ends, then by all means, say what has been on your mind: “You haven’t followed through on plans for X months/years, so I took that as a choice not to see me.” But that’s something you do for you, not to please her or abide by some unwritten rule.