He picks his girlfriends by their faces and not by how they are inside. That's why he gets hurt every time. Geez.
ご質問ありがとうございます。
"He picks his girlfriends by their faces"＝「彼はガールフレンドを顔で選んでいます」
"and not by how they are inside."＝「そして中身ではなく。」
"That's why he gets hurt every time. Geez."＝「だから彼は毎回、痛い目にあうのだ。やれやれ。」
☆「とほほ」は難しいですね。漫画などでしたら"sob!"（グス！涙）とも言えると思います。
ご参考に。
"He always chooses his girlfriends based on their looks, which is why he always gets hurt. So boo hoo!"
- "He always chooses his girlfriends based on their looks, which is why he always gets hurt. So boo hoo!"
"he" 「彼は」
"always" 「いつも」
"chooses ~" 「〜を選んで」
"his girlfriends" 「恋人」"boyfriends" や "partners"、"lovers" も言えます。
"based on their looks" 「顔で」
"he always gets hurt" 「いつも痛い目にあっている」
"so boo hoo" 「とほほ」皮肉な感じで言います。実は彼が痛い目にあってことに気にしない場合で使えます。
He always chooses his girlfriends based on how they look and not their inside. It always ends in pain for him.
ーHe always chooses his girlfriends based on how they look and not their inside. It always ends in pain for him.
「彼はいつも中身じゃなくて見た目で彼女を選ぶから、いつも痛い目にあう」
to end in pain で「結果として痛み/苦痛に終わる」
ーHe picks his girlfriends based on whether they are pretty or not. He always learns the hard way.
「彼は可愛いかどうかで彼女を選ぶから、いつも痛い目にあう」
to learn the hard way で「身をもって知る・代償が高くつく」＝「痛い目にあう」とも言えます。
ご参考まで！
アメリカ合衆国 
オーストラリア 
カナダ 
