I would probably start with the usual, dinner out and a movie. Then, depending on my date, a drive, and talking late night over coffee. From there, who knows?
To send a message to Jane, not plain you MUST meet the following criteria:
Age between 50 and 60.
Live in United States
Live within 75 miles.
Must not have messaged users looking for intimate encounters or sex.
Must not be looking for Other Relationship
Must not be looking for Intimate Encounter
Must not be looking for Activity Partner
Must not do drugs
Must not be married