These are called coincidences
You are both at an age when grandparents or much older aunts and uncles will die (or teachers or neighbors). You both get that within a few months. So what; you have thousands of experiences between, say, January 1 and May 1 of any given year. Both experiencing a death within your circle? Pretty damned typical.
You're also both at a stage in life where you may be meeting people to date or breaking up with them, or are having relationship issues with parents, or are looking for a new place to live or have mid- to lower-tier jobs and commensurate relationships with your supervisors.
You may be more aware of this because you are close friends and share more confidences, but try talking to a few other guys within your collective age group (20s) and you'll see similarities there as well.
You are also using something referred to as a confirmation bias
. This is where you are mainly seeing things in the context of whether they confirm what you're suspecting. Try approaching your ideas from a different angle. What else happened during the time period or January 1 to May 1 (or whatever time sample you like)? Did you both go out for coffee every morning? So did thousands of other people. Did you both start new jobs? So did thousands of other people. Did you both have health scares? Lose a pet? Buy a condo? Take up hang gliding? Even the hang gliding is done by thousands of people, and the combination isn't even that significant or unique, sorry.