Dear Melanie,

I am starting to like a guy that has a past with my best friend. They have never dated or anything, but I still feel bad pursuing something with him. What should I do?

The very first piece of advice I have for you is to make sure you talk to your best friend first. This may seem like the hardest thing to do, but in the grand scheme of things, it will make your situation a million times less stressful. If you know that the guy is interested in you as well, then it is easier to tell her that you and him have mutual feelings for each other and you want to pursue them, but neither of you want to hurt her in the process.

Even though your best friend and him never dated you are still treading in murky water. As a girl yourself, you probably know that girls get attached much easier than guys most of the time, and though they never pursued anything, who’s to say that she didn’t want to?

After you talk to your friend it will be much easier to judge where to go from that point on. If she is ok with it, and you can tell she genuinely is, then there shouldn’t be an issue. However, if an issue arises later, you have to know that you did the right thing and it isn’t your fault. If she says she’s okay with it, but you can tell that she’s lying, then it’s up to you to judge whether you think a relationship with this guy is worth having over hurting your best friend.

Lastly, if she straight up tells you that she isn’t okay with the situation, which I can almost guarantee she won’t do because if she’s a good friend she won’t want to see you unhappy, then you need to give her the same courtesy and maybe see how things go on the down low for a while. You don’t have to do anything behind her back, or stop talking to the guy altogether, but explaining the situation and keeping it mutual with him will give her time to mull over the situation and start to help her move on.

If there is one thing that is good to keep in mind it is that men always find reasons to come and go out of girl’s lives, but friends are consistent. Just make sure that you aren’t hurting a friend who would be there for you like no one else could if this guy breaks your heart.