Dear Shelly/Ricky

I just got out of a long term relationship. It ended really badly and it hurt my self-esteem. Since the breakup, I found out my best friend has developed feelings for me. I have always liked him, but I am scared to get too close to him. How should I tell him this and what are the appropriate steps I should take to make this new relationship work?

– Scared to take the first step

Dear Scared,

Here is an idea, how about not getting involved with your best friend! So your friend likes you, what makes it an assumption you have to get romantically involved with him at the present time? I think it is great you admire your best friend and in turn he cares about you. Realize at the moment you have a good thing going. Be content before you make things more complicated.
Your first issue is you should be grieving the loss of your long term relationship. Whether he cheated on you, you dumped him, or he let you go; you used to have someone else stable in your life and now their will be an absence. Deal with this loss. No one says you have to wear sweatpants and cry over cheesey, romantic love songs, but understanding you are an individual who can survive in this world without a partner attached to your hip!
You’ve been friends with this interest for a long time. Realize taking the next step, might feel right, but be all wrong! I am not a natural born pessimist. If you and the friend are meant to be, it will happen, but not the day after your break up of your long term interest. The worse possible scenario is you rebound into a relationship with your best friend, it does not work out, and your best friend ends up paying for the mistakes of your previous relationship. Your best guy friend should be there as a support of you moving on, not the next one you move onto. As a best friend, he probably understands this.
Best of Luck,
Shelly

Dear Scared,

First off, make sure that you get over the ex-boyfriend enitirely before you venture into something new. Nothing is a worse relationship spoiler than unresolved issues with the ex creeping into the new relationship.
This is especially true if you are going to try something with your best friend. I’m sure you do not want to get him involved in something that is doomed. My advice is to take your time with this. Sort out your feelings about the ex, then sort out your feelings about you friend. If he has waited this long, then I’, sure he can wait a little longer while you have some alone time.
Feel free to hang out with him and tell him what you are doing so he does not feel like things ‘got weird.’ Just take it slow, and the first step will happen without you even have to think about it. When you are ready, you will know.

~ Ricky