I don't think that's necessarily what it is. We're a few generations into the trend of delaying marriage, and the proverbial white picket fence is well-known as just a cliche that no one really expects everyone to have. Based on my experience as an unmarried man in his late 20's, it's not so much that the family is trying to get him to conform to a lifestyle that barely anyone lives anymore in the first place. It's more likely to be about trying to reach out to him but not having much to really talk about. (Remember the summer after high school when you had to explain to every fucking adult you knew what college you were going to, where it was, what you would be studying, etc.? It's not that most of them were pressuring you to study accounting, it's that it was a topic for conversation they figured would be good for a 10-minute chat.) They know it's rude to pry into this aspect of people's lives, but their notion of him as their grandson, nephew, etc. makes them forget that they should mind their own business. (Though I will temper this by emphasizing what I implied earlier, that a young adult isn't entitled to the privacy and discretion of an adult until they're on their own. If you're still living off the family, Grandma is free to continue asking about your dates just like she did at homecoming.)