How do I tell an older coworker I would like to become friends with him?

Question

I've been in my internship in a state-owned enterprise for six months so far, and this is my last month there. Since I started, they assigned me a mentor who would make sure I and the rest of my workmates who are on their internship as well are assigned tasks suitable for our skills.

From the beginning, I was the only one able to do advanced tasks, so I've been separated from the rest of my workmates and instead of working with them, I've been working where the permanent employees are.

I've always felt welcomed and integrated by them. During my internship my mentor wasn't the person who assigned me the tasks, but an employee who is sat next to him. In fact, he's who decided I should work around them instead of being with the rest of the interns. This man has always made everything possible to make me feel comfortable. For example, when one day I was going to be reprimanded for something that wasn't my fault he helped me telling them it wasn't my fault.

When we have nothing to do, we usually chat. And I love it when we do, because we share some interests and he happens to have the same education as me. Not to mention that he's responsible for things I would like to do in my career in the future, so I'm aspiring to become like him. One day I told him I'm good at what we do because rather than going out I prefer staying at home studying and he told me it was OK. I've consulted him about the possibility of obtaining some online certifications sometimes and he always encourages me saying I'll obtain it easily. He also gives me useful advice, and he tells me how life was before, what he liked to do when he was young, etc.

I'll really miss those moments once I finish my internship, and I really, really look forward to becoming friends with him or at least get to know him more. However, my main worry is that there's a big age difference. He's probably in his 50s whereas I'm 30 years younger (I am a male, too). So I have a strong fear of rejection because of this.

In any case, before my departure I'll talk to him in private in order to thank him for everything and tell him it was nice to meet him, and that's when I'm planning to come up with my interest of becoming friends with him or getting to know him better.

However, I honestly don't know how to ask him. How do I do it?

What's my intention

Friend is a very wide concept. When I say I'd like to become friends with him I mean I would like to keep in touch with him afterwards. But I don't just mean the typical New Year greeting or letting him know how I'm doing. I would like to keep doing what we've done so far: chat about our interests, how the industry was when he was young, ask him for advice or support... in person. That is, not limiting the contact to text messages or emails. I don't want to go out drinking or something similar. I can't even do that with people who are my age... But instead I'd like to meet in calm and formal places like a café, for example.

But honestly, my interest is mainly personal than professional. I just want to establish a friendship based on respect with someone whose career is similar to my ideal one, a role model.

Of course, I won't force anyone to do something they don't want to. But I would like to let him know I'm willing to sacrifice some of my free time to spend it with him. How to do it is what I'm struggling with.

Regarding @OldPadawan's comment

@OldPadawan has explained very well the perspective as seen from the other side, but I would like to explain what led me to believe I could get to befriend this employee. As I said, I was the only one of the interns group able to do tasks the rest couldn't. This is something that has happened to me during my life. I'm not and expert or a genius at what I do, it's just that I like researching and reading articles about what I like. I can relate to @OldPadawan because I like helping people, and I've helped many classmates back when I attended school with the subjects they found difficult.

Maybe I'm mixing concepts, maybe it's not the same to assist someone who's in your class or who is your age, but I've always found it frustrating how my help is not truly appreciated. To be honest, I expect nothing in exchange when I help someone, but when I help them and the only feedback I receive when we drift apart is a yearly text message (that's the best thing that has happened so far, the rest have completely forgotten about me) I feel empty. Being an introverted person doesn't help, so that's the best approach I can do to exchange some words with someone. I've been helped quite a lot as well, and I appreciate that help and tried to befriend the people who helped me (they all were classmates, and without the age factor), and I always failed.

These workmates of mine who are on their internship as well also believe I'm just lucky to know what I do instead of trying to ask me to increase their knowledge. They're free to do it. In fact, our mentor has recommended them to spend some time with me when I'm working. I've tried to help them many times but they just want my help when they need to finish something as soon as possible. So it's not surprise why I want to befriend someone who decides to help despite it's not his responsibility (like I said, this person is not my mentor. I'm not saying that my mentor is not doing his job properly, he just let me to seek for tasks from others) and who happens to be similar to me.

As you can see, I am someone who values people's knowledge and skills. And of course, I won't force anyone to meet in person because I value people's time, too. I hope this makes my situation much clearer and that my intentions aren't inappropriate or unusual from my perspective.

Answer 1

I'm aspiring to become like him

Seems that he did a very good job :)

As a teacher, I always do my best to help my students. Amongst other things: be patient, fair, help them understand and improve, be nice (even, and especially when criticizing their performance, because there's nothing personal!), and so on...

We do our best to make you feel great, and confident, and like (want?) to be seen as an example by our students. A good teacher isn't always a great mentor. You may learn the basics (the "technical" part), but not the human part. Seems like your mentor did both. Great job.

Now, I'll offer another point of view, the one you might consider being his, because it's mine, as it's also one of many teachers I know: don't confuse being friendly and being friends.

We like you, we love our job, we love watching you improve, and growing, and finally flying on your own. That's our reward. The extra reward is when you drop by sometimes, say hi, send an friendly email with some update on your career. You then let us know you still appreciate us doing a great job, and that your achieve that thing also because we helped you at the beginning.

A preceptor is just that: a tutor. It's not aimed at being your friend :/ Most of the time, your mentor won't have free extra time to share with you. Still, they'll love hearing back from you :)

before my departure I'll talk to him in private in order to thank him for everything and tell him it was nice to meet him

He'll probably be delighted to hear that.

... and that's when I'm planning to come up with my interest of becoming friends with him or getting to know him better.

... and that's the breaking point where I recommend that you stop before. Please, don't do that.

Tell him that you'll be pleased to give him any update about your job/career if he's willing to have any update (politely, he'll say yes). Don't offer more than the professional relationship. Show respect for the person and the good job that's been done, and don't push any farther. IF, in any case, he's interested in going one more step, he'll let you know. Just "let the door open" on your side.

When you clarify things about your current relationship, and the goal you want to achieve, it doesn't really modify the heart and the spirit of my answer. It softens the frame challenge, but not deeply what I think about how you shall act: be professional. Just that. It doesn't matter if this person has the "tutor badge" stuck to his name. He's still one (or more) level above you on the job chart, and you see him as a tutor. It means that, no matter what, treat him as you would do it for any colleague: younger or older, female or male, A or B, whatever the differences, treat everyone the same. Be nice. In this case, it means starting with small talks at coffee/lunch/break time, sharing small things that can have a personal side. Not too much. That's what I called "leave the door open". And if he's interested in the same things and has more spare time to share with you, he'll show you interest too. Never push, and always be ready to step back.

Personal note and experience: I've seen close to zero friendly teacher/student or tutor/intern relationship growing to a more personal and becoming a friends' one.

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^{As a dog lover (my students know that for sure), I often have some of them (still or former students) dropping by my desk while they're walking their dog, just to say hi. Doing that is really something I appreciate. We chitchat for a couple of minutes, give updates, and that's it... The small gesture that shows how much they liked you, and want to see a smile on your face. Another reward we, mentors, can get from our students...}

Answer 2

This is based on your entire post and not limited to the following two sentences, but when you say:

I have a strong fear of rejection

and

I really, really look forward to becoming friends with him

it makes me feel that:

1. asking him is probably simpler and has more chances of succeeding than you think,
2. your expectations towards him might be too high.

Asking him

I think you put it very well already, so I'll simply use your words. I'd say something along the line:

You do things I would like to do in my career and always gave me useful advice. We also had great chats so I would like to keep in touch with you and keep having chats in person about our interests.

I dropped "I'll really miss you" and "I'm aspiring to become like you" as some people might find it too personal, especially in a professional context. But you seem to already have a close contact with him so that might be fine.

Personally, I did something similar with 3-4 people I can think of right now, some of which are 30+ older than me, and it worked out. Probably because people don't want to suddenly break a mutually good contact.

What to expect from him

So you asked him. Now the ball is in his court. You can initiate an informal contact with him but whether or not he is interested cannot be influenced.

As I said, there is a handful of people I really admire and kept in touch with. But that is admittedly also only because I fostered this relationship. The initiative came from me almost every time. Those people were always glad to get and accept an invitation from me but usually did not send any from their own initiative.

People have a job and a life. That they really like doing something at work does not mean they'll be ready to sacrifice their free time to do more of it. Kids, sports, politics, cooking, dance class, chess, dinner with friends... you name it. If he wants to meet with you, he'll have to pass on something else. If he kept meeting with, say, one in ten interns he met in his career... he'd probably not have any free time left by now. So I think it is important that you be prepared to hear he is not interested in meeting with you regularly. And maybe not even ever again. As @OldPadawawn really well put it: don't confuse being friendly and being friends.

I personally have a good contact with all my colleagues and a great contact with some of them. But I almost never meet with them outside of work because I don't have time.