1. The first time you cry in front of him. You’ve ran into bathrooms when you were on the edge of tears in the past. You’ve cleaned up your makeup and walked back outside, pretending you were perfectly fine.

When you are actually comfortable enough with someone to be vulnerable in front of them, to let down your guard and show them your truth instead of pretending you are unbreakable, it is a big deal. It means you trust each other. It means you aren’t worried about scaring him away anymore. It means you know he is not leaving, no matter what. And that is definitely a milestone.

2. The first time you call him out on his bullshit. In the beginning of a relationship, you will play the part of cool girl, even if it’s on accident. You will try not to appear too clingy. You will try not to complain when he takes too long to answer a text or cancels plans without a warning because you don’t want to look psycho.

The moment you stop playing games is a milestone. When you are comfortable enough to tell him you’re not okay with the way he ignored you in front of friends or looked at his phone during dinner, it’s actually a good thing. It means you are able to talk to him. It means you are able to be honest with him. As long as he actually cares about your feelings and puts effort into changing the behavior, you should be proud you had your first mini-conflict.

3The first time you are naked together (in a non-sexual way). At first, you will want to jump on top of each other the second you see each other naked. Your clothes will only come off when it’s time to have sex.

But once you are comfortable, you will get changed in front of each other. You will shower in front of each other. You will cuddle naked without having it always lead to sex. This doesn’t mean you stopped being attracted to each other. It means you are able to appreciate each other’s bodies, even when sex is off the table.

4. The first time he comes to you for comfort. In the beginning of the relationship, most of the time you spend together is going to be upbeat and exciting. You are going to stick to talking about the good stuff and will ignore the bad stuff.

But the longer you are together, the more sides of each other you will see. Instead of going home and leaving him to deal with his problems on his own, you will start dealing with those problems together, as a team.

Your person might go through the loss of a grandparent, a job, a friend, or a pet. No matter what he is struggling with, it’s an important milestone when he turns to you for comfort, when he asks you for advice. That means your relationship is getting serious. It means you are the person who makes him feel the most soothed.

5. The first time he spends time alone with your parents. At first, you’re going to be reluctant to have him around your family at all. During holidays, you are going to be nervous to use the bathroom because you want to monitor the conversations. You want to make sure everyone is behaving.

But when you are comfortable in your relationship, when you have been together for a while, there will be times when your person spends time with your parents without you. He might talk with your father in the garage while you are inside. He might talk to your mother on the phone for her birthday. He might text your cousins and add them on social media. It’s a milestone once he becomes an official part of your family.

6. The first time you host guests together. There’s a big difference between attending a party together and throwing a party together. Throwing a party takes work. You have to work together on the guest list, on the food, on the decorations, on the playlist.

When you are both running around, hosting, you will see how well you work together. You will see how well you handle problems. You will see how well you get along. If you can make it through the night as a stronger couple than before, that’s another milestone.

7. The first time you throw up in front of him. In the start of the relationship, you will probably wear makeup in front of him. You will probably wear thongs and Spanx. You will probably send your best selfies instead of the first one you snapped.

When you are comfortable enough to let him see you when you are sick, it means you have reached another milestone. It means you are okay with him seeing your low points, not just your high points. This is incredibly important if you want your relationship to last. He needs to know everything about you, not just the good bits.

8. The first time your friends don’t explicitly invite him. In the beginning of your relationship, you will go out with your friends without even thinking about inviting him. A little further down the line, you will ask him to tag along if your friends explicitly ask you to bring him.

But once you are in a serious, long-term relationship, you will be considered a packaged deal. Your friends won’t have to mention he is invited because he is obviously invited. They would never dream of inviting you to a wedding or party without room for him.

9. The first time you celebrate a small holiday together. Even if you haven’t been dating for a long time, you will probably make a point to see each other on birthdays or big holidays. But when you are super serious, you will even spend the less popular holidays together.

You will get drunk together on Saint Patrick’s Day. You will color eggs on Easter. You will watch the fireworks on Fourth of July. You will buy a new mattress on President’s Day.

10. The first time you post an anniversary picture (and the second time and the third). This might not seem like such a big deal, but it means you are proud of your relationship. It means you are proud of how far you have come as a team. And you should be proud. You have been through a lot together. You have proven what a cute, strong, resilient couple looks like. TC mark


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