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Lately I feel like all the people I meet only get and stay acquaintances to mine. I don't have a huge friend group and would enjoy forming new friendships, going out more with people, etc.

If often get stuck in situations where I talk to people I met, may it be new people, people I have not seen in years, people in the gym or at work, but can't quite seem to be able to get to know these people better nor to do activities outside of where I met them.

Let's take some recent and fitting examples:

  1. At work we got like a small group (about 10 people) of young (mostly the same age group, around 2-3 years different at most) employees. We all met through multiple trainings we received at the company I work at. We also got a Whatsapp group to meet up for lunch or occasional coffee breaks. We all share similar interests and pretty much the same humor. However I can't really get them to do stuff outside of work, e.g. taking drinks, going out or something. It's hard to plan because everyone got their own life and "private" friends. One time we already picked a date for going out and some of the people said they'd come but, at the end, nobody had time

  2. At the gym there are some guys that seem to be really cool. I talked to them a few times about the lifts I/we were doing. Maybe a compliment about pretty good exercise execution here and there. One of them asked me about my warmup routine, since I'm pretty much the only one warming up properly in the gym. Here it's not that I can't meet these people, it's rather how to get to know them better and meet them outside the gym.

  3. I was out with some people from the university where I gratuated a few months ago. The event was held by the university itself, but only like 15-20 people came. I only knew a friend of mine I went there with. I had some really nice conversations and would have loved to stay in contact with some of the people. However I found myself going home with nothing, as always, because I feared asking.

Question

How can I try and ask to meet people outside of the actual setting where I initially met them, without making it seem awkward or forced? I'm always standing their not knowing what or how to say it in order to maybe get their phone number, so we can meet up some day or how/when to ask if they want to hang out.

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The work group

Of your 3 examples, the work example may be the hardest to achieve the success you want. I can't speak for your coworkers, but I know that when my work day is over, I'm not extremely keen on the idea of spending more time with the people I've just spent all day with instead of the friends/family I didn't see all day. The thing I've found to be the most motivating for me to go out with coworkers is when the event is not just coworkers. The predominant thing that coworkers have in common is the job they do. When you have a group of coworkers together, the conversations often tend to be about the job. This can turn people off to the idea of going out, because they don't want to keep talking about work.

My favorite events with coworkers are ones where people will invite guests. For example, our company Christmas party when everyone brings their significant other or board game nights where people invite their friends. When you bring outsiders into the work group, it will help to limit work-related conversations. So, my suggestion for your coworkers is to invite them out to events where the group won't be predominantly your coworkers. For example, you could host a dinner party with some of your other friends and invite one or two coworkers

The gym group

I talked to them a few times about the lifts I/we were doing.

That's a good starting point. Before you jump to trying to meet up outside the gym, build your relationship with them. I'm assuming that you see the same people often at the gym. Now that you've established conversations about your workouts, you should start to integrate other topics of conversation.

One of them asked me about my warmup routine, since I'm pretty much the only one warming up properly in the gym

A lot of people want to "get in the zone" and focus on their workout while they are at the gym. Generally, the warmup period is a little more relaxed, and I've found it to be a good time to casually converse. I used to go to the gym regularly with a friend. We would always warm up together before zoning in on our individual workouts. During our warmups we would chat and catch up on each other's lives.

Invite the others to warm up with you. While you are warming up, make small talk with them about the weather, current events, etc... After you've done this for a while, start asking questions about them (i.e. What do you do for work? How's your family? etc...). Doing this will help you start building a relationship so that when it comes time to bring up meeting outside the gym it won't feel awkward or forced. An important thing to focus on as you are building a relationship at the gym is to find common interests beyond just working out. When it comes time to ask to hang out, you can use the common interests as ideas for things to do together. For example, if you both like watching sports you could invite them over (or out to a bar) to watch a game. People are more likely to agree to come out for a specific purpose (i.e. watching a game) than they would be if they were coming out just to come out.

The alumni group

I've never been to an alumni event, but as I understand it alumni events hosted by universities are often designed to facilitate people meeting each other. All of my friends and coworkers who have gone to an alumni event went for the purpose of networking. The people you are going to meet at one of these events are likely looking to make connections, so they'll be more open to meeting again after the event.

You can be a bit more direct in asking them to meet later, but don't just ask to hang out for the sake of hanging out. As I said in the section about the gym, people are more likely to go out if there is a specific reason they are doing so. When you are talking with people at the alumni event, pay close attention to the things they are talking about. When you want to ask one of them to meet up later, focus on one of the things they've said.

Hey, I found what your were saying about your work with XYZ really fascinating. Would be interested in getting drinks sometime and discussing it further?

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Even though I agree with most of Rainbacon answer, I would like to specifically address the point about coworkers.

I, personally, wouldn't want to hang out with coworkers outside of work hours (unless I like them very much) but this might be, at least partially, linked to the fact that I have tiredness issue and I'm really not very social.

I use to work in a company where people were seeing each other a lot outside of work. They had after-work poker, after-work football, after-work beer, etc... They also had a "pétanque" (an outdoor game similar to Bocce) every lunch break on summer.

One thing that, I believe, was key to the success is that it had nothing do to with work (except for the coworker). It was mostly games where people were having fun and didn't talk about work.

One other thing was that, all off this activities where just after work (or during the lunch break) and was, at least, less than a minute walk of the work place. So, going to see if the proposed thing was fun didn't necessitate effort or time from people.

Finally, one thing that can have been at play is that all of these after-works were regular happenings. The beer thing was every Thursday with everyone who wanted to join. On summer, the beer thing became the football thing and it was, again, every week. And, as I said, the bowling was every day for the lunch break. (maybe this point is irrelevant but, in doubt, I preferred to specify it).


So, I don't know how you could get people on board with that but making sure that:
1) They don't have to make effort to go there
2) They can expect to have fun there
Is probably a good start. Then you can work on having it becoming a regular and expected thing.

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