Dear Mel,

Recently my best friend asked me to go on a date with him. While I’ve known him forever and we’ve casually hung out before, I have no idea what I’m supposed to do on this date! He recently told me how he feels about me and I’m super excited, but I don’t know how to get over the first initial awkwardness. Help me!

-K.A

Contact Melissa Puppo at [email protected].

Dear K.A.,

    This seems like a very exciting step in your relationship, so don’t let the fact that you guys are best friends make it awkward. That should make it easier!

    You both already have something that other new couples have to worry about — comfort. You’re way past the initial stage of opening up to one another while staring at each other, then at your food, then back to each other during dinner on that first date.

    You can now get to know each other on a deeper level and see if you enjoy it enough to date him. Sure, if things go well and natural things like kissing or holding hands come into play, use that as a sign to see if you’re feeling it. You might find that you enjoy spending time with him and are experiencing a new relationship that you never knew could exist.

    If you don’t feel comfortable or if it’s not what you thought it would be, don’t worry! It’s perfectly fine to tell him you aren’t into it. If you guys are best friends, then he should understand. If he goes on a rant saying you can’t be friends anymore, then obviously he isn’t as good as a friend as you thought.

    Don’t make it out to be a big production. Whatever you do, just test things out. It will probably come natural.

                              XO —Mel