How to signify to a coworker I'd like to become friends?

Question

TL;DR

I'd like to befriend a coworker with similar hobbies and values but I'm afraid I'd either sound awkward or flirty. How can I make him understand I'd like to become friends?

Situation

I've been working in the same company for 9 months now. There's a coworker I met around the time I started that I recently got to know better after attending a programming boot camp he organized. There were 6 of us at the camp and we learned quite a bit about each other during our lunch breaks, where the atmosphere was more relaxed.

I'd like to befriend this coworker, but there are two main issues that prevent me from doing it quite naturally:

• He's a divorced man who's almost 20 years older than me and as I'm a very sociable woman. I'm afraid my sympathy would come across as flirting with him, and I really don't want that.
• I don't have many friends anymore, most of them left after graduation and I want to make new friends. It's been a while since I last befriended someone and I suspect that coming to see him and saying "Hey! You seem nice. Let's be friends!" may not work.

What I tried so far

• I invited him to have lunch together at work. I accompanied him to buy some food and we came back to the office and ate with two other colleagues who extemporaneously joined us. I told him afterwards that I spent a nice time and he answered saying we could do it again on the days where he's free. This happened very recently so we haven't had lunch together again since.

• Although this is not primarily driven by my will of befriending him, I send emails or come to see him whenever I'm stuck with an issue related to the language he organizes boot camps about. This gives me the occasion of asking him how he's doing, and he doesn't seem bothered by the question.

Question

How can I signify to my coworker that I'd like to spend more time with him as a friend, without sounding awkward or flirty?

Answer 1

Be honest and direct.

This situation is a bit easier to handle than the alternative where you are trying to make a friendship at work into something more.

For work-related lunches, etc, I see no need to do anything differently than what you have done: you have an open invitation to continue organizing lunches together. That's pretty normal coworker behavior, and common even for coworkers who would otherwise never see each other outside of work-related functions.

However, if you want to invite this person to something else outside of work you have a shared interest in, it's fine to make your expectations known. Unlike another answer that suggested you just share your hobbies together platonically, doing hobby activities together is also a normal part of starting a non-platonic relationship.

Invite your coworker to whatever activity or event you might have shared interest in, express briefly that you don't want to be misinterpreted as looking for anything besides a friend, and let him respond.

Possible scenarios:

• You are on the same page, no problem, and no further worries for you.
• He was uncertain what you were looking for and now you will have clarified and avoided future awkwardness.
• He had other interests and now can politely bow out if those are his only interests.

Only the last one really comes with a negative for you: you might have lost a chance to have a buddy, but at the same time you've avoided awkwardness in the future.

Answer 2

Last time I did it, I did it through the hobbies. We shared a love for a hobby activity, and I invited her to join one. It worked.

Thinking about why I might be reluctant to join a younger woman for something, I might be worried about possible romantic intentions. I might be afraid of being socially awkward (and I am often). I might not want to get into a one-on-one situation. I might want some assurance of enjoying what happened. I might want to maintain the ability to back out with no hard feelings.

So, the reason to get together was completely non-romantic. Any awkwardness could be at least glossed over by concentrating on the activity. It would be a group activity, so nobody would be semi-required to interact with any other in a non-structured way. The activity would be fun. If she hadn't liked it, she could have thanked me and said that she was not interested in that activity, and continued refusing other offers until I got the hint that she wasn't interested (seriously, I'm happily married because I couldn't recognize a brush-off forty years ago).

It was much like working together, in some ways, and so wasn't much of a step. Semi-task-oriented activities are great for meeting others.

Answer 3

I've had success making friends with coworkers through hobbies. Both myself and my coworker play badminton so we started meeting at the same gym to play, granted in this scenario we are both straight men so there was very little risk of romantic intentions but I still think if you would like to be friends outside of the office you should look at what you have in common outside of the office, otherwise it's fairly simple to be friendly acquaintances in the office.

To address your concerns that this may come off flirty, the age gap should help to lessen the risk of that but to be sure just try to keep things professional, be careful about touching and perhaps avoid discussion about relationships.

Answer 4

TL:DR You need to find value in him and he in you that is outside of attraction, whether that be a common colleague that you both hate or a hobby or even a conversation. If it the value is based on attraction then you risk pushing towards a relationship. And if there is no value, then you will just remain polite work acquaintances.

You need to find something in common, outside of one anthers company. As in if all you do is go out to lunch together or go and check in on him at work, there is a high chance of this being misconstrued as either flirtation OR work friends.

The other facet is just doing things together. This typically works better for strengthening a bond that is already there. And once you two are comfortable as friends this is absolutely something you should do. BUT When used from the get go, it comes off as relationshippy (Which you are trying to avoid).

As for direct actions. I would keep up the in work contact, going to lunch ect and getting to know each other. But as another answer said be careful of "Flirty" subjects and touching. Then once you have gotten to know each other well enough to find common interests, suggest you do those things.

As for the specific conversation re: just wanting to be friends. That is something that I would leave until you are moving in the wrong direction and need to correct. At which point, you need to be firm that you value him as a friend and don't want anything more. Though if he values you for things other than attraction, then this will never get there.

One little extra tid-bit friendship is usually something that happens a bit more spur of the moment, (A common feeling, or hobby) not so much something that is forced like this. As in people try to make friends, and force it sure, but not usually with 1 specific person. That is usually reserved for dating and relationships. Also it is much easier to befriend him as a part of a friend group than it is on your own with such a targeted approach.