I really wonder if there was any particular meaning in the kind of souvenir he gave me during his business trip.
ご質問ありがとうございます。
「彼はどんなつもりで出張[土産](https://eikaiwa.dmm.com/uknow/questions/36232/)を私にくれたんだろう?」は英語で「I really wonder if there was any particular meaning in the kind of souvenir he gave me during his business trip.」と言います。
また、「同僚の男性が出張のお土産といってハンカチをくれました。お土産はお菓子とか消えるものが普通なのに」という部分も英訳したいなら、そうすると「A male coworker gave me a handkerchief as a souvenir he got during his business trip. When you think of souvenirs you normally think of stuff you can consume.」になります。
ご参考になれば幸いです。
"What did he mean by giving me this souvenir from his business trip?"
"What did he mean by giving me this souvenir from his business trip?"
"what did he mean~" 「彼はどんなつもりで〜だろう?」
"by giving me this souvenir" 「土産を私にくれた」
"souvenir from his business trip" 「出張土産」
[つもり](https://eikaiwa.dmm.com/uknow/questions/54649/)についてもっと詳しく知りたい方はクリックしてください。