It’s not worth risking your friendship if you aren’t completely sure of what you want out of pursuing the relationship.
If you’re hearing phrases such as: “You’re like a brother/sister to me” or “I don’t want to jeopardize our friendship” or if your friend is asking advice on another person he or she is attracted to, you shouldn’t even think about dating the friend because chances are your friend doesn’t share the same romantic feelings for you. You both should be going into the new relationship hoping for serious results.
At this point, it's easy as pie to tell when he's being weird because he's working too much or because he's kind of pissed off at you because of something you said or if he needs help because he's probably an alcoholic who won't admit it.
As friends, you’ve already passed that test with flying colors.
If you’re going to take the risk of changing how you interact interpersonally it needs to be for the right reasons.
If you are going to date you have to treat your new partner as a girlfriend/boyfriend not just a friend.
You should only date a friend if taking your relationship to the next level is a serious decision, and if you decide to do it you have to go all in—ask the person out on a real date—one where car doors are opened, flowers are purchased, the whole nine-yards.
The guy who slept with you and then stopped calling you for no reason?
If his last girlfriend texted him 4,000 times a day, you know not to text him 4,000 times a day and thus, only text him 3,999 times a day. One of the hardest parts about dating someone new is "oh my god, who even is this stranger?! He already knows some of your #issues and is fine with them.
The advantage of entering a relationship with a friend is that you’re already comfortable around each other and you’ll bypass any awkward stage that most new couples go through.
You most likely have similar interests, are in the same social circles, enjoy the same hobbies and you already know the other person cares about you.
There’s nothing that anyone can do about what goes on in your head about your new dating adventure, but the goal is to keep those things from coming out.
Once those thoughts turn into actions, things go awry.
The embryonic stage of your courtship, relationship or whatever you call it when you first start dating is quintessentially the most important time.