On the one hand, many people are uncomfortable navigating the tricky terrain of a friendship that turns romantic. On the other hand, a romantic relationship with friendship at its base can be a very strong, long-lasting one, with a rare degree of trust and openness. Make the invitation, but give your friend as much room (and time!) as they need to answer, with the knowledge that they may say no. If you give them this freedom and are genuinely willing to accept “no,” it’s unlikely you’ll jeopardize your friendship.