When I’m around my friends, I usually listen to their stories, and ask them questions about their lives. When I’m around my friends, I usually listen to their stories and ask them questions about their lives.

When you are listing two or more things in a sentence, the last entry must always start with "and" or "or" depending on the situation. For example: When I'm with my friends, we usually play basketball, go to the movies, or walk around town. When I go outside, I always take my wallet and keys.

When I’m around my friends, I usually listen to their stories, and ask them questions about their lives. When I’m around my friends, I usually listen to their stories and ask them questions about their lives.

"When I’m around my friends, I usually listen to their stories, ask them questions about their lives." <--- is actually okay, BUT grammatically incorrect. It gives the feeling of giving an unfinished list, and trailing off without finishing the sentence. Not uncommon in speech. It's sort of like ending a sentence with the て form of a verb (～話を聞いて、人生について質問をして。)

When I’m around my friends, I usually listen to their stories, and ask them questions about their lives too. When I’m around my friends, I usually listen to their stories and ask them questions about their lives too.

The sentence feels incomplete without a connector; “too” makes it flow naturally

ALSO POSSIBLE: When I’m around my friends, I usually listen to their stories, and ask them questions about their lives. ALSO POSSIBLE: When I’m around friends, I usually listen to their stories and ask them questions about their lives.

原文も可能です。 / The original text is also possible.

I like catching up with them, even if it’s no hasn't been that long since I last met them. I like catching up with them, even if it hasn't been that long since I last met them.

“it’s not been” is awkward; “hasn’t been” is the correct contraction.

BETTER: I like catching up with them, even if it’s not been that longhardly any time has passed since Iour last met themeting. BETTER: I like catching up with them, even if hardly any time has passed since our last meeting.

質問:「I」という言葉を同じ文章で2回繰り返すことは避けましょう。 （話すときは大丈夫ですが、英語の書き方と話し方は少し違います）SUGGESTION: When writing, avoid repeating the word "I" twice in the same sentence. (This is okay when speaking, but written and spoken English are slightly different.)

Sometimes my silly behavior totally gets me into unexpected situations, and it feels a bit awkward, but that’s fine when at least they laugh and don’t blame me for it. Sometimes my silly behavior totally gets me into unexpected situations, and it feels a bit awkward, but that’s fine when at least they laugh and don’t blame me for it.

Unless you specify who or what the silly behavior is acting upon, it will act upon itself.

Sometimes my silly behavior totally gets me/us into unexpected situations, and it feels a bit awkward, but that’s fine when at least they laugh and don’t blame me for it. Sometimes my silly behavior totally gets me/us into unexpected situations, and it feels a bit awkward, but that’s fine when at least they laugh and don’t blame me for it.

Sometimes my silly behavior totally gets inleads to unexpected situations, and it feels a bit awkward, but that’s fine when at leas long ast they laugh and don’t blame me for it. Sometimes my silly behavior totally leads to unexpected situations, and it feels a bit awkward, but that’s fine as long as they laugh and don’t blame me for it.

“leads to” fits better "as long as” is the natural phrasing

Sometimes my silly behavior totally gets us into unexpected situations, and it feels a bit awkward, but that’s fine when at least they laugh and don’t blame me for it. Sometimes my silly behavior totally gets us into unexpected situations, and it feels a bit awkward, but that’s fine when at least they laugh and don’t blame me for it.

MORE SUCCINCTLY: I also often ask my friends for advice about my life. MORE SUCCINCTLY: I also often ask my friends for advice.

NOTE: You can safely delete the phrase the "about my life."

I used to tend to avoid asking for advice before for some reason, but now I often tell my concerns or worries to my friends with honesty. I used to tend to avoid asking for advice for some reason, but now I often tell my concerns or worries to my friends with honesty.

It's not wrong, but since you already put "I used to," adding "before" sounds redundant

I used to tend toBETTER: At first I avoided asking for advice before for some reason, but now I often tellexpress my concerns or worries to my friends with honestfrankly. BETTER: At first I avoided asking for advice, but now often express my concerns or worries to my friends frankly.

I realized how awful it is keeping my concerns or anxietyies hidden in my heart. I realized how awful it is keeping my concerns or anxieties hidden in my heart.

"my anxiety" = general feeling of anxiety, focusing on the feeling itself "my anxieties" = specific instances of anxiety, focusing on the reason for the anxiety (ie. anxious because of school, anxious because of work, etc) I think you meant the latter but maybe not...?

I came to realized how awful it isit is a burden to keeping my concerns or anxiety hidden in my heart. I came to realized it is a burden to keep my concerns or anxiety hidden in my heart.

After I realizeding that, it became easier for me to show my weakness and true feelings to my friends. After realizing that, it became easier for me to show my weakness and true feelings to my friends.