Popa,
I wouldn’t trust myself on how I feel after one date (barring exceptional circumstances, such as clear hashkafic differences).
Being a shadchan is tough, because some people need nudging (I don’t do much shadchanus because I don’t do the nudging part well), but when you do, you get blacklisted on YW.
There are a lot of happily married couples who credit the shadchan’s stubborness for their shidduch.