Life seems boring, don't know how to proceed

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Over the past year, I basically got mentored by a friend on how to live life. She was quite like the average poster on 4chan, but maybe a bit more depressed and lazy. Anyways, she basically taught me to only depend on myself, and that the only person who could make me happy is myself. Eventually, she disappears from my life and unlike previous friendships, I didn't feel sad. I learned what I needed from her, and felt at peace.

Now that I'm no longer being mentored by her, I've begun to socialize with others a tiny bit more, especially with a friend I met a few years ago. This person was a girl I met at a summer program, and we went on a few dates, but never anything serious. We remained friends, but during the time I was being mentored I was very distant.

I'm now at a point where I don't know if I should try and create a strong bond with this girl or stay distant. If I try to make a strong bond (or even date, cuz we both realize that's an option), I may become dependent on another person for happiness. If I stay distant, I might miss out on what could have been.

I've been at peace with myself for these past few months, and I don't know if it's worth the risk to trust other people. On the same hand, it's been a long time since I've seen people romantically and had close bonds with people.

Any advice is good, all ears here.