1. Whether he believes in god. It may not seem important when you’re in your 20’s and everything is smooth sailing, but life gets very hard. When you struggle through job loss, health issues, family emergencies — how is he going to cope? Is it compatible with the way you will cope?
2. The names of his parents and immediate family members. These are the people who grew up around and formed him into the person he is today. If you want to understand him, you have to understand them.
3. What he’s like when he’s sick. If it’s been all rainbows and sunshine, you still don’t really know him.
4. What he listens to in the car. Along with the big stuff you want to make sure you’re digesting all the little commonplace things about him. You know what he puts in his coffee, what his morning routine is, what he listens to on the way to work, and what kind of shampoo he uses (especially by smell).
5. Who he voted for. Agree or disagree with his political beliefs, they’re an important part of his value system and thought process. You should know what kind of leaders he likes and what draws him to them.
6. His childhood pet’s name. You’ll want to tell each other the stories of your life, especially what it was like for them growing up.
7. His career goals. Where does he want to go and how can you support him in getting there? He’s going to spend most of his waking hours at whatever his profession is, that’s too much time for you to be completely clueless about it.
8. What you can’t stand about him. If you’ve only seen things in him that you love, you’re not past the honeymoon phase.
9. What his friends are like. At this stage you should know who his friends are, what they do when they get together, and what kind of people they are. When he tells you a story about one of his friends, he uses their first name because you know who they are.
10. What he’s like when he’s raging mad. When he’s at the end of his rope, does he still treat people with respect? Does he ever flip out? Has he ever been violent?
11. Whether he wants children. It’s okay if this milestone is far off in the distance, as long as you’re on the same page about whether it’s something you’re both interested in.
12. How much money he makes. Additionally: how much he saves and what his debt situation is like. Obviously these are not conversations you have right when you’re getting to know someone, but if you’re contemplating a future with him, you need an idea what that future is going to be like. Money matters when you’re considering legally attaching yourself to someone’s financial situation forever.
13. How clean he keeps his home. Long after he picks up before you arrive, is his “resting” state of affairs something you can handle? If he’s stupid messy and that chaos stresses you out, you have something to think about.
14. How often he prefers to have sex. Sex is the physical bond that keeps your attraction alive in a relationship, if either of you is being rejected all the time it’s going to cause some wear on their happiness. The healthiest relationships aren’t between people who have a huge mismatch in libido.
15. What he’s like on vacation. Some people go on vacation because they want an adventure and spend it in exciting cities seeing and doing new things. Other people want to park their butt on a beautiful beach and not move for 7 days except to pick up a new drink. You can compromise and do things you both enjoy, but you should know what their preference is.
16. What cheers him up when he’s sad. This is super important, because you need to be able to speak this language to him in order to support him through difficult times.
17. Where he wants to plant roots. Does he like big cities or small towns? Does he want to move away from the place you met one day? Where does he want to raise children if you have them?
18. What he absolutely needs to do in order to unwind. Some people need to come home and turn on trashy reality tv or play video games or be outside or get a good workout in every single day. He won’t be able to feel complete with you unless he can be himself, including whatever mechanisms he’s created in order to veg out.
19. What his issues are. Everyone has something. There’s a sore spot in all of us that’s made up of un-healed emotional baggage. You should have some idea of what this is for him and be willing to walk with him as he figures it out.
20. Whether he’s totally over his exes. You don’t have to dwell on his life before you, but it is important to know for sure that he’s ‘over’ her and not using you as a crutch (or worse, to make her jealous).
21. Whether he respects people who are different than himself. There’s an easy way to find this out: look at how he treats customer service people who help him out.
22. What his views on couples therapy are. It’s an incredibly handy tool for working through rough spots, but some people are totally opposed to ever trying it. Best to find out now.
23. Whether he’s comfortable giving you space. You need to know what kind of social life you’re going to have and whether it’s going to fully overlap with his social life. Is he the kind of guy that encourages you to go on a girl’s weekend trip? Or will get get jealous and ask you to check in constantly?
24. What he considers cheating. It’s going to be a problem if one of you thinks flirting with your regular barista is totally fine and the other thinks that crosses the line. You have to be on the same page about what’s cool and what’s going to be a problem for the relationship.
25. Whether you really love him. It can’t just be the idea of him — or of being in a relationship that’s moving forward. You have to be know that you love him and that the feeling is mutual and that you’re both going to put in the work to make each other happy.