Meeting the parents – yes or no? It is usually worthwhile. It does not mean a commitment. At all.
It can be beneficial to you. You can get a better sense of who they are and their family and context. You will see them with their family – how they interact with their parents, how their parents interact with them.
It is beneficial to them too. They can put a face to a name. They can get a sense of who their child is dating and it can make them feel more comfortable with you.
If it is not the typical practice in your community, it does not mean that you shouldn’t consider it. It may be out of your comfort zone, but that does not mean that you shouldn’t do it.
When to meet (at what point during the dating)? At any point really. Remember, meeting the parents is not a commitment. In some communities, the parents meet the young man before the first date, when he comes to pick her up.
For how long and where? That all depends. It does not have to be that long. But it could be. You might come into their home for a few minutes before a date. You might meet at a neutral place like shul or for coffee. It might be that they come to the car for a few minutes.
What to do in this meeting? Ideally, you and your date should be there together. Discuss beforehand what this meeting will be like – for how long, where, what. Let the parents take the lead. Understandably, you might be nervous, but try to get into a natural conversation. Some parents get nervous too and ask bizarre questions, just answer as best you can. In their nervousness, some parents may not know how to end a conversation and you may have to be the one to do that; wrap up politely.
Note: sometimes people get nervous in such situations and this may not fully reflect who they really are.