It's a two-for-one "Family Matters" special this week!
My friend's mother is recently single, and I saw her on Tinder. I want to ask her out. I know it's weird, 'cause I've known my friend for so long, and she's, like, 25 years older, and she might not be interested. But I think she's really interesting, and I wanna do it. Do you think my friend will be mad?
My Friend's Mother Is Hot
Dear My Friend's Mother,
Whoa! Total Mrs. Robinson vibes.
First of all, the age difference is irrelevant if both parties agree. Maybe it's crazy, but it's not impossible. Still, you gotta ask your pal if it's cool. I'd like to say you and the mother are adults and should do whatever you want. But a child/parent relationship is in the balance here, so don't be surprised if your buddy is skeeved out by the whole thing. If so, you'll have to respect their perspective and back off.
On the other hand, if your friend is super evolved and says, "Why not?" then go for it! And then you two ought to be real frank about some boundaries regarding your friendship and their family unit. Who knows? Maybe you'll have a cool, modern, happily-ever-after kinda ending. Fingers crossed.
I'm a bisexual man. I've had this girlfriend for a little while, and I recently got drunk and fooled around with her stepbrother. I don't think he realizes that she and I have been a little serious together. I don't know what to do. I don't want to be with him, but I do want to be with her.
Come clean — like, right now — and apologize. It doesn't take a rocket scientist to know that this situation is effed up. Not only did you cheat on your GF, but you crossed a pretty sensitive line by getting intimate with two members of the same fam. There's a good chance this relationship is over.
Not sure what's up with the bro not knowing about you two, but you need to chat with him ASAP, too. I'm guessing he'll feel pretty shitty for making out with you. Either way, you need to tell him that your encounter was a mistake. Be direct and clear; he might have different expectations than you do.
If your girlfriend does want to stick it out with you, be patient and understanding about the potential awkwardness for her and her stepbrother. Trust can take time to rebuild, so tread carefully and be prepared for some distance at first. In time, maybe you can get back to where you were.
But I have to be honest: I'm not optimistic about this.