Everything changes when you enter your late 20s. Your interests, your friends, your free time, your goals. Everything. You finally realize (or at least you hopefully realize) that it’s time to grow up and start thinking about the future instead of holding on to the wild and crazy party animal you were in your early 20s. This of course happens at different times for everyone, but ultimately for most people, it takes place at some point in your late 20s.

As you start to figure out your *realistic* wants and needs for the future, it would probably be a good idea to share your thoughts with your partner — if you have one. Not because once you’re in your late 20s that means you HAVE to start thinking about marriage and kids and babies and settling down, but because you should be telling your significant other what you’re thinking (even if it’s nothing at all) to make sure you’re on the same page.

A lot of people in their late 20s are looking for serious relationships. They don’t want to waste time with someone they have no chance of ending up with. Sure, not every relationship will work out. Not every marriage will work out. But you can at least do everything in your power now to make sure the person you’re with seems like the right person for you.




That means addressing those hard questions about your future. What if you want to have kids and your significant other doesn’t? What if you want to spend your extra money on vacations and spoiling your kids and your partner wants to save? What if you want to get married and your significant other doesn’t? You aren’t crazy or ‘moving too quickly’ bringing these topics up. They’re pretty legit. Do you want to find this stuff out after a couple years and have to start all over again in your 30s?

Here are 11 questions you should ask your significant other if you’re in a long-term relationship in your late 20s (or whenever actually). Sure your ‘page’ might change as life goes on, but it’s at least good to make sure you’re on the same page right now.


1. Where do you want to live?

Maybe you’ll find you both want to live in the same place, maybe you want complete opposite lives, or maybe you want different things, but there’s room to compromise.


2. What is your future dream home like?

In addition to talking about WHERE you want to live, you want to talk about HOW you want to live. And by want, I mean want, because although you might make it big and be able to afford your dream home, this will always be a stretch. Unless of course, your dream home is totally affordable because you’d rather put your money elsewhere.


3. What is your future realistic home like?

It’s great to discuss dreams, but you also need to discuss reality.


4. Do you want to have kids?And if so, how many?

Usually when one person says they don’t want kids, that means they don’t want kids. And if you are the person who wants kids, don’t assume your partner’s mind is going to change eventually because they’re in love with you and will do whatever you want to avoid losing you. Yes, it might change, but it also might not. After all, if you want kids, do you really want the parent of your children to be someone who has verbally expressed that they don’t?

It’s also good to discuss how many kids you each want. Raising children is expensive.


5. When do you want to have kids?

Before 30? Early 30s? Late 30s? When you have a certain amount of money in the bank? Never? It might sound crazy to talk about, but you don’t want to – for example – resent your partner later in life for making you wait for something you wanted years ago.


6. How much ‘money in the bank’ would make you happy?

Everyone has aspirations. Share them with each other.


7. What are your thoughts on expensive weddings and engagement rings?

Ask their opinion on these things in casual conversation. Maybe you’ll find that damn, you do not see eye to eye on these things at all.


8. Do you want to get married?

Because this could be a problem if you both have different answers to this question.


9. Do you want to travel?

Or would you rather live life on the couch in yoga pants watching Netflix?


10. If you saved up a decent amount of money, what would you want to do with it?

You should probably make sure you both have the same thoughts on this just in case one of you wins the lottery.


11. Where do you see yourself 10 years from now?

This is arguably the most important question of them all. Taking you out of the picture, where does your partner see him/herself in 10 years? Are they married? Do they have kids? What do they do for work? Where are they living? You can find out a lot about a person’s ambition, goals, drive, and interests just from answering this question. You can also find out if they’re totally NOT thinking about their future if they don’t have an answer to this.


There you have it — the world’s hardest questions to ask in a relationship.

Once you ask the questions, though, the job isn’t done. You’ll need answers. And if you’re not getting answers, you may be dealing with someone who is immature and not growing with you. Or you may be dealing with someone who just wants to tell you whatever he/she thinks you want to hear to avoid issues. OR you may be dealing with someone who knows their answers don’t mesh with yours, but your relationship isn’t as serious to them, so they would rather not talk about it.

Sure you and your partner may love each other, but sometimes love isn’t enough. This is why these questions are so important.


Hi I’m Sam. I made this website in 2011 and it’s still here! I'm the author of the humorous self-help book AVERAGE IS THE NEW AWESOME. I like pizza, French fries, barre, spin, more pizza, more French fries, and buying clothes. Follow me on twitter & Instagram at @samanthamatt1... and on this site's meme account on IG at @averagepeopleproblems. OKAY GREAT THANKS BYE.

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