Under what circumstances would a man choose to remain a bachelor?
When he is not confident enough to think that he'll be able to trust a partner; When he would rather deal with his life's finances and get his career going before choosing to try that sort of thing; When he is fulfilled in life, and just doesn't think there could be any more room (Although I'd disagree with this). There are other circumstances, but they are far in between, I'd say.
Maybe you should ask yourself, "Why NOT remain a bachelor?" Then depending on what you come up with (which could be nothing!), you'll be surer of the answer.
Marriage is life-style choice. It is not a requirement to be "happy". If a person enjoys being single they should continue being single. The last thing one should do is get married just for the sake of getting married. Life is a personal journey and each of us gets to choose how we want to live. We are responsible for our own happiness.
The key to being happy is to know thyself, love thyself, and trust thyself. If you know what you want or what makes you happy then go after it.
My significant other (of 20+ years) is a bachelor by choice. We've found no reason to marry yet share a very fulfilling life -- he has his interests and I have mine and then there's those we share. We both consider marriage sacred and most of our friends are married with grown or nearly grown children. We each accept the other just as we are, manage our own finances and property and enjoy one another's families. Anyone who chooses not to marry, be it man or woman, has just chosen a lifestyle that suits their wants and needs for many different and varied reasons. After a period of time single persons become very independent (and I personally am very set in my ways) and perhaps this is an answer to the question.
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