What does this sentence containing 「いい歳したオッサンが」 mean?

Question

私は今20代後半ですがとても子供っぽく落ち着きがありません。（夢中になると特に）いい歳したオッサンが自分と正面から向き合ってくれた人と本当の意味で向き合って話が出来ないという現実に絶望しました。

Source: https://komachi.yomiuri.co.jp/t/2019/0624/903959.htm?g=04

Does 「いい歳したオッサン」mean he's referring to himself as 'this old man', or is he talking about his own father or just some random middle aged dude ?

いい歳したオッサンが自分と正面から向き合ってくれた人と本当の意味で向き合って話が出来ないという現実に絶望しました。

I understand this sentence as:

I came to a depressing realization that I cannot have a real, honest talk with someone who goes out with me based on my outer face (public face) according to some old man

Am I understanding this correctly ?

Answer 1

I agree with you that this sentence is a bit hard to follow, but the only reasonable reading is that this オッサン refers to himself. The sentence contains a few nuanced words:

• いい歳（年）: a fixed phrase that can be understood "an age that is old enough", but you can take that the whole wording 「いい年して」 corresponds to "despite one's age" (see What is the meaning of the phrase いい年こいて?).
• オッサン（おっさん）: literally this word means a man who is around as old as an "uncle to a kid", but especially as a recent slang it roughly means a guy who is no longer in his youth. On the Internet people began to say 30越えたらおっさん "you're おっさん after age 30" since a little while ago, so this is the vibe this word carries.
• 向き合う: literally "face" but often specifically means to engage seriously, sincerely with a thing or person (= soul, personality etc.)

So, I think what the sentence means would be like:

I came to a depressing realization that I'm not mature enough at my age to be able to really do the same for someone who did try to understand me honestly as a person while talking with her.