So, I have two non-imaginary friends whom I will call J and P. I'd guess that J is in his late thirties and P is in his middle forties. Now, a quick recap of their lives:
J works as a senior engineer at Microsoft. He is not married, has never been married, and has no children. He lives happily (as far as I can divine) by himself. He has no girlfriend. He likes volleyball, board games, and video games.
P works as a technical writer at Microsoft. He is married to a woman in Canada but separated, lives with his only son, and has a girlfriend. He has various published articles, books, and games under his belt. He has been in divorce proceedings for half a decade, ever since his wife decided she didn't want him around anymore. Under Canadian law, if he doesn't pay his wife $3,000 a month in spouse support, which he can't afford, he has to settle, which means giving her complete ownership of their retirement account, house, and all of their belongings in Canada, valued in total between $400,000-500,000 CDN. He says she'll make a fine second wife for anyone who is interested in neither intelligent conversation nor sex and doesn't mind marrying someone who has no conscience.
Both J and P are very smart, pleasant people. My pessimistic view of the world tells me that I can basically choose between ending up like P and ending up like J. In this case, if I have the option of having loved and lost and never having loved at all, I will wholeheartedly choose what's behind door #2. Of course, those are not the only possible outcomes... I just see them as probably being the most likely for me. And, the prospect of ending up like J doesn't really bother me. Maybe it should.