Is it possible to send an email to the same contact that has two records in a custom object ?

Hello community.

Is it possible to send an email to the same contact that has two records in a custom object and that by segment filter should include both records?

There is a custom object with the relationship that exists between a client and a vehicle. That object has the necessary information of the client and the vehicle. It is required to send an email to the client 60 days before the end date of the vehicle's warranty. But a client can have two vehicles that meet the condition of being within those 60 days, when making the segment it will only take one of the records, so the client would only be receiving the notification of one of the vehicles.