Friends or More?

Should you date your friend? Or perhaps more accurately, is it worth the risk to date your friend and possibly lose the friendship if it does not work out?

Lots of solid relationships state that an important component is their friendship. Sometimes they start out as friends and some times they don’t, but always they insist that their significant other is their best friend who they tell all their embarrassing stories, hopes, and fears to. So one might think dating a friend would be a great idea because that aspect is already there and has built a strong foundation.

Of course once you cross that threshold from just friends to more than friends, its near impossible to go back. This has got to be the strongest reason people with crushes on their friends give for not pursing it. They don’t want to lose that friendship and closeness. They would rather have them in their life as a friend then risk becoming closer and then ending up with nothing. Sometimes friends don’t want to mess up the group dynamic by dating or sub consequently breaking up.

The thing is if you’ve naturally floated into the territory of daydreaming about one friend in particular then it may be worth digging into. He already knows your interests and dislikes pretty well. You already know about his bad habits and future plans. If you know all this and still can’t stop thinking about him then it may be time to start pushing the friendship boundary and see if he feels the same way about you.

If you don’t try, you’ll always wonder. You may become self conscious or doubt yourself more if you start thinking, well why hasn’t it crossed his mind yet to date me!? Maybe he didn’t think you’d like him back, maybe he has too much on his plate and wouldn’t be able to give you the effort you deserve. All I know is that it’s an unhealthy mental state to be wondering about all the possibilities and insecurities without any sold facts. It will give you a peace of mind to hear his sides of things no matter the outcome.


  1. This sounds like dangerous territory to me. Friends with ‘benefits’ could easily shift to no longer being friends at all. Although if one of you was in a relationship when you became friends, and that relationship ended, that could work, if the friendship entered up a notch … I’m no expert on this, married for 35 years to the man who has become my best friend.


  2. Love this! Well thought out, well said!

    My thoughts on this are, if you’re such good friends, then hiding what you’re actually feeling from him/her does a great disservice to the friendship itself. Best to be completely open and honest with them, an admittedly difficult thing to do in this case!


  3. I think this can only be answered on a case by case basis. No 2 people are going to have the same depth of friendship or react the same. There a lot of questions to ask yourself before opening that can of worms, like: Do you know your friend well enough to know whether or not they would be comfortable knowing about the crush? Sometimes just the information can mess up a friendship or cause people to start acting different. Would you be ok with a rejection? How is this going to affect how you feel about them if they say no?


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