Dear Prudence

Dear Prudence Uncensored: The Boyfriend’s Daughter

Every week, Danny Ortberg and Nicole Cliffe discuss a Prudie letter. This week: the boyfriend’s daughter.

Nicole: Oh, boy. Well, my first suggestion is to be light and funny and acknowledge the weirdness with a joke

Whatever seems appropriate in the moment.

Also if you can change the plan, I recommend the meeting be “see a movie together and get dinner after”

Danny: i want to give this LW permission to say “I am not ready to meet your daughter” if she doesn’t feel ready, by the way!


Nicole: OH absolutely

Danny: three months and “I really like him” is not that significant an investment

Nicole: I just spotted the 3 months

And feel like you definitely should push that back if this seems overwhelming

Danny: yes! it’s totally fine to say “i’d love to meet your friends some other time but i’m not ready to meet your kid unless and until we’re more serious”


Nicole: And don’t feel like you have to try super hard, teenagers are different than small kids and tweens

Light and breezy is good, make sure they know you’re not making a run for New Mommy

But yeah, waiting for a more serious conversation about your future is good


(I am good w teens)

Danny: i know very few teens, i have no idea

but i would just say the trick is to keep your expectations super low

Nicole: RIGHT

Danny: you could be the most fun and interesting, laid-back-yet-energizing presence in the world

Nicole: The movie suggestion also helps bc you can just … talk about the movie if things lag at dinner

Danny: and she might just be bringing “i don’t like that my parents are divorced or that my dad’s dating a 25-year-old” energy to the table

Nicole: Totally

Danny: and you have to respect that! let her hate you

Nicole: Or find you silly

Also fine

Danny: this is a real problem with age gap relationships: you’re young enough that this teenager could reasonably bully you


Nicole: Hahahahaha YOUTHS

Danny: also ask your boyfriend a few questions about how he’s talked to his daughter about you


has he introduced her to new girlfriends before? how did that go?

Nicole: RIGHT

Danny: if he’s like “oh i’ve never done this before and i’ve only mentioned you a few times and every time she’s said ‘i hate her,’ ” he has done insufficient prep work

Nicole: In general, talk to him some about the future AND about his kid

Danny: or conversely if he says “yeah i just introduce her to girls whenever,” that’s another red flag to watch out for

Nicole: woooof yes


Danny: someone who is good at dating as a divorced parent will have a plan of action


he’ll take primary responsibility for dealing with his child and keeping you apprised of what you are and aren’t responsible for

Nicole: And if he is very bad at it, what an important data point

Danny: and if he seems kind of bewildered or confused or hasn’t given it a lot of thought or looks to you for guidance here

there is a reason he’s dating two decades younger

but assuming everything is reasonably well-thought-out in advance

be friendly and relaxed, don’t try too hard to seem cool or make her like you

Nicole: This doesn’t have to be a disaster

And “a little awkward but civil” is a great outcome

So keep those expectations low

Danny: yes!

awkward but civil would be great