1. Sex – how much of it to have and how often and with whom and what you like about it and what you don’t. It’s a continuous unfolding. But a fun one. So enjoy the process.
2. Where to live – in an apartment? In a house? With roommates? With your parents? Alone? How much is location worth? How much is privacy worth? It’s likely going to take quite a bit of trial and error to work it out.
3. Short-term career objectives – What’s reasonable to expect from a workplace? How much money should you be making? Do you want a 9-5, or freelance work? The fluidity of the job market can be paralyzing.
4. Long-term career objectives – What do you want to do long-term? Do you have to start working on it now? What is your ten-year career plan? How flexible is it? We’re all a little foggy on the details.
5. Friendships – How do you maintain them after college? How do you form new ones? How much effort do you put into Skype calls vs. meeting new people? There’s nothing easy about friendship after college
6. How to relate to your family – you’re not a kid anymore but you’re not a fully established adult either. So you’re going to flip-flop a bit in your role as a son or daughter or sibling and that’s perfectly normal.
7. Money – how do you prioritize it? How do you save it? How do you talk about it? This is perhaps the biggest taboo of your twenties and it’s one you’ll always be a little curious as to how other people are handling.
8. Food – what do you need to stay healthy, now that your body doesn’t metabolize pizza the way it used to? How much salad do you have to eat, really? Which fad actually diets work? Which juice cleanses definitely don’t?
9. Personal morals – which fine lines are you absolutely unwilling to cross? What happens when you accidentally cross them? How do you forgive yourself? How do you move on?
10. Personal style – how old is too old for a nose ring? Are you supposed to just lop off your hair and get a bob at 25? How do you portray yourself as confident and mature but also fun and uniquely yourself?
11. Drinking – How often do you do it, at each stage of your twenties? When does going to bars become pathetic? When does casually drinking alone become unhealthy? The exact amount of alcohol we’re supposed to consume each year of our twenties is hopelessly vague.
12. Where to live – Do you bust your butt to make it in a city or stay home and enjoy a slow-paced life? Are you drastically missing out if you choose one over the other?
13. The dating world – Do you want to play the field or settle down? Do you want a partner in crime or the yin to your yang? Dating takes a lot of trial and error and our twenties tend to be heavy on the error.
14. How to achieve balance. Trying to find the middle ground in terms of work, love, health, drinking, managing money and just about anything else in your twenties can feel like a never-ending task that you never quite
15. Sexuality – How fluid is your sexuality? How interested are you in experimenting with it? And once the experimenting’s over, what do you stick with? How do you identify yourself? There almost seems to be too many options at this point.
16. When to hold onto love and when to let it go. When is it worth it to fight harder and when is it time to just give up and go home?
17. Lifestyle – How much consistency do you need in your day-to-day life? How about variety? How do you want to prioritize work vs. relationships vs. personal time in order to achieve the lifestyle you want?
18. Travel – How much traveling do you want to do each year? Are you willing to prioritize it over other potential milestones, or are you fine with letting it take the backburner?
19. Exes – You’ve accumulated one or two of them by now, but what do you do with them? Stay friends with them? Block and delete them? Ignore them for the rest of eternity? Everyone seems to have a different strategy and you’re still figuring out yours.
20. Mental health – and how to maintain it. What happens when you can’t afford the therapy you need? How do you keep yourself in balance through lifestyle choices? What, if any, help do you need beyond that?
21. Physical health – how often are you supposed to see your doctor? How about your gynecologist? And more importantly, how do you lock down the health care necessary to see those people in the first place?
22. How much independence you want – Do you like to have a core circle of people you rely on when things get tough? Or do you prefer to go it alone? How much space do you want for your own life and your own pursuits, vs. how much are you willing to prioritize important relationships?
23. Taxes. How do we do them. No, seriously. HOW.
24. Jealousy – and how to manage it. What happens when you don’t get that important promotion but your coworker does? How about when your best friend meets the love of their life and moves in with them, leaving you alone? How do you manage those feelings in a healthy yet mature manner?
25. Existentialism – WHAT DOES ANYTHING EVEN MEAN? Unless you’re in a serious relationship with a major world religion (and in many cases, even if you are), this question is going to berate you mercilessly throughout your twenties. And, let’s be serious, probably for the rest of your life.