I'm nearly 50 and an extrovert and I've found that healthy and fulfilling relations are a function of reciprocity.
I'm willing to engage with someone 3x and see if they'll reciprocate. If not, I move on--no hard feelings, just realizing it's not a mutual fit.
This rule has served me immensely well in my friends. As a result, I have nearly no loose friends--just very tight, reliable connections.
"Never let a task to be accomplished be more important than a person to be loved."
"The primary feeling in any interaction should be love."
"Observe and serve."
This does not mean failure to speak only truth in kindness as appropriate, or to set boundaries when necessary. I think Jesus Christ's example of understanding, truth, and kindness are ideal for us all.
Also as some have hinted here, being a good listener, asking questions, caring about others' background and well-being in general, being humble, willing to share when appropriate, and looking for the good and things to appreciate in others, and ways to serve, can go a long way. Interesting volunteering opportunities (where you would meet people as a side-effect) might be found at https://justserve.org if available in your area.
This is a great start! You’re already doing what most people find the hardest: making the first move.
Grabbing coffee, and even going out to dinner, aren’t good activities for making deep connections. They’re too short and too routine. They can work, it’ll just take longer, and you will have to work harder to make sure conversation is meaningful.
I think the best way to make real friendships is to go on a weekend trip somewhere together. First of all, you’re spending days together instead of hours, but more importantly, you’ll have a shared experience to remember. You get to see what someone is like not only during activities and meals, but also during downtime.
Weekend trips could be awkward if it’s just one on one though, so if you don’t have a group, the next best thing is doing an activity together. Figure out a shared interest, then invite your new friend to do something you’d both enjoy. Maybe it’s a concert, talk, hike, whatever. Do that a few times and your new friend will associate you with that activity. Next time they’re going to a concert/talk/hike or whatever, they’ll invite you to tag along.
2. You may actually be full of sh.t (nobody's perfect). Only life and rarely a very close true friend can give you proper hints (or lessons which are often quite expensive, but that is what builds your character and makes you you in the end).
>Are You Your Friends’ Friend? Poor Perception of Friendship Ties Limits the Ability to Promote Behavioral Change
https://journals.plos.org/plosone/article?id=10.1371/journal...
What we tried to do was basically inviting all our neighbors over, always being nice without trying too hard. At first some would not even say hello back. After a while we developed relationships that are not very deep yet, but we’re getting somewhere. It takes time, a lot of time.
What I would suggest is that you try many different people (neighbors, fellow parents from school, work colleagues) if one relationship doesn’t pan out. Eventually you’ll find someone with whom you will “click”. For me the best relationships I got was with the former work colleagues, we just kept in touch and hanged out after work.
I will accept almost every social engagement with people I like, though.
So: maybe it's not you.
(2) Be Childlike in your approach to life and relationships
(1) Honest Living
If your boring (and I don't know if you are), its probably because you stopped pursuing things that you wanted and excited you for something safe. Boring people also mask their emotions when speaking to people to avoid rejection.
To find people you genuinely connect with, you need to express yourself fully. Honest expressions will make you more polarizing, and you will experience rejection. But the people you connect with will be much deeper because they see who you actually are.
Honest living usually means some therapy or self reflection to identify the things in your life you stopped purusing. A simple litmus test: you are in a social situation and see a person you find attractive. Do you make excuses for not talking to them or go and talk to them, openly stating your interest?
(2) Childlike
Children play until they get hurt or get in trouble. Do you approach relationships with this attitude? Is your heart open to loving other people even if it hurts and they reject you?
You have to risk the relationship - the very thoughts you fear, the thoughts "Oh, I could never ask that, they'll hate me."
Those thoughts. You have to voice them.
It's the only way to maintain intimacy and reveal who you truly are.
One of them is that this kind of people are generally in the minds of their friends/acquaintances. And one of the reasons there is that they see them as very good listeners during conversations. They match their conversation style, they confirm what they’ve been talking about with feedback and this sort of behaviour that tend to help people build trust and friendships.
I’m not done with the book yet, but I can see many things relating to what I generally practice. And I’ve got good friends :)
We tend to not get personal and if you don't have deeper more meaningful conversations with someone you can't really become "friends."
I've only had a few friends my entire life and I've lost most of them.
Many people don't think twice about friendships (of any kind). It's them.
You are not their top of the list attraction (of any kind). It's you.
But then too, when you are lucky enough to find someone who really clicks with you, do ask them to critique your approach. Sadly in many cultures including the US, this is just "not done". Not considered appropriate. Even when you ask. That's so sad. No wonder we are lonely.
For gelling with new people and bringing them into your own circle, it's good to understand that it's a numbers game too. Figuring out social groups that you enjoy should always be the main goal. I have real life friends who love climbing, and we already budgeted time for climbing, so we usually hang out before or after a session and it hits all the same. Similarly, online friends who like building video games like me can sometimes spare the time to play or develop together.
Increasing your surface area in this way is a great way to start! As you get acquainted with more people, the chances that you have at least one person to hang out with at any time increases greatly, and in turn that they will want to hang out with you.
Disinhibition is a social lubricant. We are so used to being safe because that's what the workplace requires, that we've lost the ability to be disinhibited around closer relationships. People who can be disinhibited and show their flaws are really attractive. But it doesn't come free, some people will reject you more. And that's ok.
Treating relationsips non-transactionally, helped me. Sure, sometimes I might feel a bit disappointed. That's a hazard of para-social thinking. Relationships have asymmetries. Hence the friendship paradox: https://en.wikipedia.org/wiki/Friendship_paradox
Maybe I’m a boring person?
Well half of all people are more boring than average...But mostly adult lives are complex. You probably don't rate as highly as someone's child, partner, or established social circle. These are long term relationships. Good luck.
Anecdotally, I desire to hang out with people who share my interests and want to do similar activities that we both enjoy.
I’m a few years removed from college now, and it’s highlighted to me just how special living closely with people of similar age and interest does for one’s social life. Once you spread out, gain dependents, work, etc… it’s much more of an effort to stay in touch.
Just because someone doesn’t reciprocate your effort to connect doesn’t necessarily mean they don’t want to hang out with you.
A colleague might be a fun character telling stories over a beer but also professionally useless.
If a colleague invited me out for a coffee - and we didn't really know each other in the office - I would be suspicious as to their motive.
Trying to make convo circumstances and process perfect cannot solve mental issues or deeply ingrained habbits. Not quickly anyway, perhaps not at all. But for damn sure, it's thinking in the right direction!
I am currently wanting to apply this "even" to friendships but run into the issue that people "don't have time".
There are quite a non-trivial number of people who reach out to me (mostly old friends/coworkers), with whom I wouldn’t want to engage. There are multiple reasons, but it fundamentally always boils down to any social interaction with them being an opportunity for them to compare themselves with me, and making me feel inferior, by explicit comments or by some sort of virtue signaling. I’m not even sure they realize it, and it’s also possible it’s just in my head. Regardless, that’s how I feel.
I am not a complete sociopath, so just declaring upfront that I do not desire to meet with them is bad taste in my morals, so I simply ruthlessly decline every single invitation, until they get the point and stop reaching out. It’s puzzling to me how sometimes a person might reach out for YEARS before giving up (on a perhaps 2-3 month basis for 2-3 years), asking for a call or to meet up, and me every time shutting them down with “I’m busy”, “I’m traveling”, etc.
Make no mistake, if I were to “cave in” and meet them up, it would immediately be an opportunity for them to flaunt their financial/marital/career/athletic success in front of me, by comparing themselves to me, so no, no pity. Example: a “friend” who made $20M from an extremely lucky IPO had the nerve to tell me “why don’t you just pick a good company that’s going to IPO soon and make a lot of money like me? A couple years and then you’re done, it’s easy”. No shit lol. This is a person who insisted for YEARS to meet up, after I started the process of declining any invitation. Fortunately he seems to have moved on now, but never say never.
Rather than try to change how that person responds to you, you can either work on being ok with how little they initiate, or you can put effort into other (or finding new) relationships where people will initiate more.
People also go through busy and less busy times - so maybe try again with this person in 6 months and see if things are different.
There are so many different kinds of people (with so many different preferences), that I really think your time is better spent finding new people that you click more with, rather than trying to change yourself.
You don't "fix" it, you just fine-tune your behavior models.
Make of yourself something that people need and/or want (which is often something they'll eventually outright signal that they're missing). Don't make yourself dependable, but desirable.
Empathy and compassion are fickle resources because if you are superficial about expressing them, people will notice.
Sound advice and expertise are nice but limited in scope and frequency, and require some reputation and trust building.
In most informal contexts most people are prone to oversharing to a keen ear. So become an active listener, pretend to be genuinely interested (but not necessarily empathic) about people's experiences and throw in something relatable to them on the way, pretend to be more stupid than them, grease their egos while playing an innocent contrarian, and eventually they'll think you're a great person and invite you to their secret boring, pretentious and utterly tasteless wine drinking clubs. If that's what you want then you win.
People are busy and don’t think about others most of the time. Most live in their own world.
If they get an invite, they’ll often be happy to mix things up and meet. Then most go back to their normal routine.
Give off relaxed and breezy vibes. It’s easy to sense when someone is trying too hard. Most don’t want an another obligation in life, so they don’t want another thing they need to be bothered by. However, a friend that is casual works out better.
Amount of time between hanging out has naturally gotten further apart. Allow yourself to be okay with this aspect.
Don’t take things personally. Be your natural and genuine self.
Good luck!
Learning how to be emotionally vulnerable is key to actually connecting with people. The book "Models" by Mark Manson is a pretty good primer on the importance of emotional vulnerability to connect with people. It is sort-of a dating advice book, but I've found it helpful for making regular friendships and connecting with my own family as well.
Another thing that is helpful is learning how to communicate assertively- which is the opposite of being emotionally manipulative. The book "When I say no I feel guilty" is particularly good introduction to assertive communication. A lot of people only learned emotionally manipulative communication, and will be avoided by almost anyone that sees that for what it is.
Counter-intuitively, not being desperate is critical. Be willing to judge if someone is worth your time, and be willing to disagree with people or say no, without letting the fear of being rejected control you. The same authenticity and vulnerability that will make people really connect with you, will also drive some people away, and that is totally fine. The goal is not to be friends with everyone, but to make good friends with people you are compatible with.
Therapy can often be helpful for developing all 3 of the above skills.
Lastly, take the initiative to make things happen. Invite someone to do activities several times before expecting them to reciprocate. People tend to be busy, shy, stressed, etc. - just because people don't reach out doesn't mean they don't like you.