The Timeline Of Guys You’ll Probably Date Through Your 20s And Beyond (And What You Mean To Them)

Boys will go, and boys will stay, and boys will probably always come back. This is the timeline of men you will go through, who you are to them and who they are to you. If you are lucky enough to have all 4, I promise it will get better at least I hope.

1. Boy Next Door (15-18)

YOU ARE FOREVER HIS GOOD GIRL. Puppy dog first love. This love is naive, its pure. This is probably the first time you liked someone and they liked you back. This kind of purity in love, only exists when you are young. This is completely innocent, you still wonder if a boy could ever love you that simply again.

This is after school and video games. This is the guy you called on his house phone, talking to his mom waiting for him to pick up. This is the guy you thought you were going to end up with before sex, love, drugs, and alcohol got in the way. It was easier when we were younger, they say. You graduate high school, you either separate or try to make it work at the same school. But, you are no longer the same. High school had rules and boundaries. University is all about freedom.

You both need to explore and find out who you are without each other. At the time, you think you will be making a huge mistake. You are now thrown in pool of froshies and fraternity guys who all want only one thing from you. You will never have that purity, that innocence, that simplicity ever again. But, this is good for both of you. You won’t see it right away, but if it is meant to be you will come back to each other. You might come back to each other a few times, because there will always be that comfort with him. But you won’t be the same people, if you do come back. Which will be your ultimate catch 22, because that person will always be a memory to you. You may not like who they have now become.

He might also hate how you have changed even more. In his mind you will be seventeen FOREVER, HIS GOOD GIRL. He will always be the boy who used to walk you home. You both only exist in your memories. You two are nostalgia at it’s core. When you are with him no matter how old you are, you will always feel 16. If you ever get back together with him , it will be like going back in time. Which could be refreshing to have something so pure again, or it could feel like going backwards.

2. College Sweetheart (18-23)

YOU ARE HIS BEST FRIEND. This is your classic “real first love,” no one will ever compare connection. You thought you had this before with the first guy, but you were wrong. He is your college sweetheart. College is all about finding yourself, and while you were looking for yourself you find him along the way. This relationship is filled with high fives, beer pong, and brunches. You were young and you had nothing, but time my friends. You grew up together, you did everything together. He was a part of all your firsts. He even shaped who you have become.

He will always be a part of you, because there are too many memories to pretend to forget him. He was your BEST FRIEND. Your relationship was effortless. You worked together, you went to school together, you went to the kegger on friday night together. His friends were your friends and vice versa. You knew each other so well you didn’t have to say anything, you knew what the other one was thinking.

He gets you, and you think you know him better than anyone. You are in this beautiful stage of your life, where you can believe anything is possible. Your dreams aren’t crushed yet. Your mind is still hopeful. You haven’t been jaded by the real world yet. You talk about your dreams with him, and he motivates you. You believe in each other, because you have no reason not to. College is this wonderful soul searching time in your life, you change drastically over these years. You find yourself and lose yourself again, almost every weekend you do this. But, he never changes. He does this with you.

You are young enough, that you still live in the moment. You don’t have a checklist of a 5 year plan, hell you don’t know what you are doing 5 days from now let alone 5 years from now. This love was real, because it was solely about the people you are. It isn’t about their salary, or where they live, or how many kids they want or don’t want. It is about right now, and all they want is each other. This relationship was easy, because your life was easy. It was convenient because he was always at the same places you were without asking him to be. It seemed too good to be true.

It wasn’t perfect, it was the perfect mess. you get drunk and fight with him. You love and hate each other at the same time. You get over it, before the party ends. Youth can be so forgiving. Your love is unconditional, because he is your best friend. You can get through anything together, because you always have. Then one day, you wake up and the dream is over. Graduation is here. Everything you used to love about each other you, now all of a sudden you fear. You thought you can make it through anything, now this is anything coming for you guys.

3. The Man Child (23-28)

YOU ARE HIS EMOTIONAL PUNCHING BAG Did you hear that? No, I was trying to ignore it too. The real world is calling and we are both not ready for it. If you happen to survive postgrad with your best friend relationship, this is the true test. You lived in this beautiful fantasy world we call University. Then before you know it, time flashes through your eyes. You no longer have time to stay up partying all night, then head to the library with him the next day and throw a Hail Mary on your midterm.

You can’t stay up talking all night, sharing each other’s secrets until daylight hits. You have graduated, you have to pretend to be a real person now. You have bills, and no longer covered with student health benefits. He gets a real job, he hates eventually. Seeing each other is no longer effortlessly, because you don’t run on the same schedule anymore. You start to live in your memories, because that’s all you have left of him. He is no longer your best friend. This part of your life is over now, and you have no idea how to make this relationship work anymore.

All of sudden you can’t sleepover on a Tuesday, because he has “work”. A job, that he reminds you every day about how much he hates. He starts to settle, and is pushing you away for morning sex. You watch the boy you used to know, drown into a sea of mediocrity. There is nothing you can do, while you are still chasing your dreams; he has slowly given up on his and on you as well. While trying to help him, all you are doing is pushing him away. The resentment slowly starts to build up.

He constantly reminds you of how “tired” he is, or how “those days are behind him now” or how he is a “grown up”, because he has a real job. He used to be your best friend. Now you have become his EMOTIONAL PUNCHING BAG. He is going through his quarter life crisis, this isn’t his fault. You are going through this as well, but you are just avoiding it better than he is. This is a very common thing called “ Post Grad Depression”. We are forced to grow up., but we have not left our university mind set.

Some of us hold onto to university with dear life, Peter Pan syndrome. Others slowly miserably accept this change . This is an awkward time where we are no longer reckless college students, but we aren’t exactly adults either. We all handle this shift differently. In university life, we were all in the same boat. This is the first time in our lives that we have really left our comfort zone and it is terrifying. Most of us feel like if we don’t land our dream job within 6 months of graduation, we have failed.

This isn’t true, but with this sense of failure we tend to lash out on our partner.You always hurt the people who love you the most. He has no one to lash out to but you, and you no longer have anyone to vent to. You used to tell him everything, you never thought he would be the one you have to vent about . All of sudden you feel bored and married, which is crazy because you two used to be the most fun at the party. Your relationship used to be your escape, now you feel trapped . This is the “struggling” point in his career. Where it is all work and no play. AKA no more time for attention for you.

You tell yourself this is a phase and we will get through it, because we can get through anything. It’s hard, because some days feel like yesterday. Then you wake up and realize it’s not. He’s going to work at a “soul wrenching job” just to pay the bills, and you are wishing he is going to show up and sit next to you at the library. You are now living in your memories. The highlight of your relationship is in the past. All you hope for is fleeting moments, when he is the person he used to be. 5 seconds ago you were on top of the world with him, until you both actually entered the real world. You say he’s changed, he says he has grown up. And that’s the end for you two.

4. The Older Guy (29-50)

YOU ARE HIS PRINCESS This man, and let me emphasize on the word man here. He is the first guy in your life who is NOT a boy. This will be a nice fresh change from number 3 the Man Child. This will be a relationship like no other for you. For the first time in a relationship, you will not be equal. You will not be in the same life stage.Typically men, who date women much younger than them treat their woman like a PRINCESS.

Why? Because they can. They are much older than you, they probably have more money than you. They aren’t stressed like “the Man Child”, because they are already in a quite comfortable place in their career. They just want to find a typical nice girl to take out and spoil. If these men are dating quite younger women, they still might have some growing up to do on their own. They were probably players in their past, but with their friends getting married, having kids, they are finally ready to be committed to a girlfriend.

Although, they are getting old. They don’t want you to remind them of that.. One of the reasons they are most likely going out with you is, because “you make them feel young”. They may not be ready to leave the night life yet, that is why a woman in their early to mid 20s is perfect for them. This man gets stability with a relatively young woman. Without the added pressures of getting married and having children by next spring, with a woman his own age. However, as perfect as this new man may seem. No one is perfect. You may never pay for a single dinner, because the struggling part of his life is over. But you will probably never be his best friend either. Hanging out with his friends will almost always be awkward for you, because you are 24 and almost a decade younger than him.

His friends are married and some even have kids. These are not the same couple group hang outs you are used to. You probably won’t become best friends, with his friend’s girlfriends. You won’t form a friend group with this man. Your friends and his friends will be separate. It will be hard for his friend’s wives to like the young girl he is now dating. They definitely won’t like that you probably have hot girlfriends your age, that you are bringing around. With the age difference, this relationship can never really be equal.

You are in your quarter life crisis. You are most likely still finding yourself. And he simply is, not. He works hard and plays hard that is why he is with you. At the same time, he plays by his rules. It is always about his schedule, never yours. Again, kind of like the “Man Child” he likes to remind you he works. He believes since he treats you like a princess, AKA he provides for you. It is on his terms. When he feels like it, thats when he will do it.

Being a princess can be great? But remember in fairy tales princesses never got much of a say? You are like his living doll. There is a reason the princess always wanted to escape.