10/07/2026
This involves some high school drama nonsense that a guy my age really shouldn't have to deal with, but maybe I'm missing something here. So, here I am looking for some perspective. I'm a forty-five-year-old guy, and I share a seventeen-year-old daughter and a fifteen-year-old son with my wife, who's forty-one. My wife's best friend, who's forty, has two daughters of her own, aged eighteen and fifteen, and they moved to our town about six years ago. Since then, my wife and her best friend haven't been so subtle about pulling for the two fifteen-year-olds to end up together.
I'll be honest, I find the whole matchmaking thing weird and low-key creepy. About two years ago, my wife's best friend's youngest daughter actually developed a crush on our son. My boy talked to me about it, and he made it clear he didn't have any interest in her whatsoever. We sat down and discussed how to tactfully but firmly let her down, which he did. But she didn't stop there. She's approached him again a number of times over the last couple of years. Each time, he's reaffirmed his lack of interest, but she hasn't taken the hint.
Fast forward to this past summer. My wife's best friend's oldest daughter turned eighteen, and her parents went all out for her birthday. They planned a whole weekend of festivities and events. One of the main events was a couples' dinner for the oldest daughter and all her friends. The younger daughter really wanted to go to the dinner but didn't have anyone to go with. She asked my son if he'd accompany her. He's a nice kid, so he agreed to go, but he made sure to establish they were going only as friends and just this one time.
So, they went together to the dinner. Afterward, the group watched the movie '10 Things I Hate About You' together. It was my son's first time seeing it, and he commented that he thought the Heath Ledger singing scene was cool. This detail is important for what happens later. Now, my business partner throws a huge Halloween party every single year, and it's always a big deal. All our employees are invited, along with close friends and family members. The party requires a costume, and there are always prizes for the best individual, group, and couples' costumes.
My wife's best friend and her family are obviously invited every year as well. This year's Halloween party is happening tonight. That brings me to the reason I'm writing this. About a month ago, my son was at school, minding his own business. Suddenly, my wife's best friend's younger daughter comes towards him in the hallway. She didn't just ask him out; she performed a whole song and dance routine right there in public, ending the spectacle by asking him to be her date for the party.
My son was so frustrated by the public ambush. He reiterated, loudly enough for everyone around to hear, that he isn't interested in her like that at all. Of course, it being high school, some of the kids laughed at the rejection. She ran off crying, and unfortunately, she's been bullied pretty badly by other students because of the incident. My wife's best friend is livid about the whole situation. She thinks our son owes her daughter an apology for rejecting her so publicly.
My wife actually agrees with her friend on this. She thinks that, at a minimum, our son needs to defend the girl against the bullying at school. My son, however, has pointed out that for two years he's told her he isn't interested and reiterated it over and over again. At this point, he feels like it's kind of harassing to him, and he doesn't think it's his role to defend someone who's been harassing him from other people's mockery. I've got to say, I agree with my son on this one.
My wife and I haven't seen eye to eye, and we've had a number of disagreements about it since it happened. Well, things have intensified in the last couple of weeks because another girl from school, who the best friend's daughter apparently doesn't like, asked our son to be her date for the Halloween party. My son actually agreed to go with her, and they're planning a pretty dope couples' costume together. This new development has really pi**ed off my wife.
She thinks he shouldn't go to the party with another girl out of respect for her best friend's daughter's feelings. I think that's ridiculous. He shouldn't have to put his life on hold. I'm planning on driving them to the party myself tonight. My wife now doesn't want to go to the party at all. She's saying I'm an as***le and that I'm raising our son to be one too. So, AITA?