What are you looking for in a relationship?
CO-sa CER-chi in U-na re-la-TSIO-ne — stress on 'co-', 'cer-', 'u-', 'tsio-'. 'Relazione' has four syllables: re-la-TSIO-ne.
A direct and mature question — appropriate when the date is going well and both people seem serious. Shows you are not just passing time.
'Cerchi' = you look for (second person of 'cercare'). 'In una relazione' = in a relationship. 'Relazione' is the standard Italian word for a romantic relationship. This question is bold but increasingly common as Italians become more direct about intentions.
Stai cercando qualcosa di serio?
Are you looking for something serious?
More direct — shows you are clear about wanting something real
Cosa è importante per te in un partner?
What is important to you in a partner?
Focused on qualities rather than intentions — slightly softer
Hai delle aspettative per questa serata?
Do you have any expectations for this evening?
Meta-question about the date itself — honest and slightly daring
While older Italian dating norms involved longer periods of ambiguity, younger Italians (particularly in cities) are increasingly direct about intentions. Being clear about wanting something real ('qualcosa di serio') is respected as mature and honest — not too intense.