The concept of an afterlife is the single biggest marketing gimmick of Christianity. Most other religions do not play on people’s emotions in this way.
The link explores the question of loved ones, children and parents, who might not have made the cut. Of course, the later generation may be in hell. Either way, will the dead person in hell reunite with loved ones?
We could ask an expert, a person who has spent a career studying the Bible. The link author provides detailed answers. To summarize, it is unclear in the Bible whether or not souls go to a hell and it is not known if or how souls have a relationship with other souls. Like in most important questions, the Bible is not clear. Ancient writers were not addressing questions of 2018 but those of their time.
If seems to me dishonest of the faith to offer up this benefit of an afterlife if it doesn’t provide some solid information about this promise. The cleverness of the promise is apparent, make up you own definition of the afterlife and use it. Believers are not to doubt it is there.
There is another alternative, critical thinking. If you think about the origin of the theory of afterlife, you can quickly see there is no evidence of it. You can also see a broad sweep of people benefit from keeping the myth alive.
Grandma and Grandpa did not have an afterlife, but they had a life. That’s more than enough.