American English Corrections

Last Night

I had dinner with four of my friends last night. They are former co-workers Quondam is too "big" of a word for most people to understand. :) of mine. I 'll meet up with them about every about three or four months. The last time we met, I met them in the May, which is when the sakura or "cherry blossom" season takes place.

Three of them are retired. They are over 20 years older than me, in fact, they look like my parents. or more naturally as, "in fact, they could be my parents." since you mean they are around the same age as your parents. They are very wise, intelligent, gentlemanly and humorous. and I always learn various things about the life from them. Their advice is useful to me, so I'm always looking forward to meeting with them. I had a good time in last night.

After dinner, we parted, but I went to a bar with one of them. She is a co-worker that has shared in both in good and bad times with me at work. At the bar, we got caught up Very good use of vocabulary. "to get caught up" is a word I consider a little more advanced than most words non-natives use. :) in talking about each other's lives until half past 3 am. I talked a lot, and I had a  good time.

Very well done. Keep up the good work. :)

I had dinner with four friends last night, former colleagues from my job. I meet them about every three or four months. The last time we met was in May during Sakura season.

Three of them are retired. They are over 20 years older than I am; they look like my parents. They are very wise, intelligent, [gentlemanly] and humorous, and I always learn various things about life from them. The advice is useful to me, so I always look forward to meeting them. I had a good time last night.

After that, we parted, but I went to a bar with one of them. She is a colleague that shared both good times and bad times at work with me. We caught up with each other's lives until 3:30 in the morning. I talked a lot. It was a good time.

~~~

Sounds like a really nice time!

I wasn't sure about "gentlemanly"; we usually don't use that word in English to describe women. Maybe "well-mannered" would work? I don't want to change your meaning.

Also, I had to look up "quondam" -- it's a rather obscure word! But it translated to 昔の, so I interpreted it to mean that you worked with these people a rather long time ago. Sometimes we say "old colleagues" or "old friends", but we have to make it clear that we don't mean "aged".