Building persuasive user experiences is like a relationship and you need to treat it like one. So, what do you want? A one-night stand or a lasting partnership? There are three common challenges when engaging users with a product: Sign-up challenge: seducing your users, first-time use challenge: falling in love with your product, and ongoing engagement challenge: staying in love. Your approach to engaging users should be appropriately adjusted to the relationship you have with them. We will examine the three stages of a user relationship and what tools are appropriate to use for each challenge. This article is a summary of Anders’ talk on designing with persuasive patterns at the Push Conference 2015.