Something is wrong with Ushio, though. No normal person hears "I'm down bad for someone else" and thinks "That makes me interested in you!" She's gotta be into NTR or some bs.
More realistically, she’s a woman in her mid thirties who’s using a matchmaking service. She wants a partner but probably hasn’t had luck or trust with the men in her daily life.
She’s probably attracted to Ishizumi’s honesty, loyalty, kindness, and selflessness to put the feelings of someone else before his own. It helps that he’s got good looks and he has his life together with a good job and a good work/personal life balance.
If the thing you value most in a partner is stability then those are all great traits and it’s a great first impression - especially because he’s also single and technically only has a crush on someone else rather than any actual dates or commitments.
I think any progress to get Ishizumi out of his weird, “I only date someone when they’re blackout drunk and don’t remember me.” thing he has going on with Reina is a good move forward for the story. It’s a fun premise, but as the manga’s gone on and started to do character exploration of its leads it’s actually a pretty fucked up situation when it’s not being a gag romcom.