Do you enjoy my company?
ti PIA-ce la MI-a com-pa-GNI-a — stress on 'pia-', 'mi-', 'gni-'. 'Compagnia' has four syllables: com-pa-GNI-a.
A slightly vulnerable question — asking directly if they are enjoying being with you. Shows confidence and vulnerability together.
'Ti piace' = you like (it pleases you). 'La mia compagnia' = my company. 'Compagnia' means company in the sense of being together, spending time together. This is a sweet and honest check-in that Italians find charming.
Ti stai divertendo?
Are you having fun?
Simpler but genuine — makes sure they are enjoying the evening
Spero che questa serata ti stia piacendo.
I hope you're enjoying this evening.
Softer — expressing hope rather than asking directly
Sei contento/a di essere venuto/a?
Are you glad you came?
End-of-date version — invites a clear positive reflection
Italians generally express care for others' experience directly — asking 'ti piace la mia compagnia?' is read as thoughtful and genuine, not insecure. It shows you are oriented toward the other person's happiness, which is an attractive quality in Italian romantic culture.