Dear Davida,

About a month ago, I broke up with my boyfriend of two and a half years. Before that, I was with another boy for about the same length of time. My question is, since I spent the entirety of high school and then some in long-term relationships, how can I get back into dating? I haven’t been on a first date in a long time and I’m not sure what to expect or how to go about it. I’m especially nervous about the awkwardness of starting a conversation with a new person. How can I get over my anxieties and get back in the game?

Signed,
Benchwarmer

Dear Benchwarmer,

Finding your feet after ending a lengthy relationship can be some scary stuff. The first thing you need to do is ask yourself if you’re truly ready to begin dating again. Depending on the person and the nature of the previous relationship, finding the right time to start looking again can take anywhere from weeks to years. Whatever you do, don’t rush yourself. If you feel you’re really ready, start slow. If you find someone you’re interested in, get to know them. Strike up a conversation, develop a friendship, and if you think they have potential as a date, ask them if they might like to go out sometime. Start with something easy that will encourage conversation, like dinner or coffee. Remember to be confident and optimistic, but don’t hold the person to unrealistic standards, and do not to compare them to your ex—this is an opportunity to start fresh and begin a new adventure with someone totally different. And if the first date—or the second, or third—doesn’t go as you’d hoped, write it off as a learning experience and move on to the next person. At first, it will be painful and awkward, but eventually you’ll get a clearer idea of what you’re looking for, and with the right amount of time and Applebee’s two for $20 specials, you’ll find it.