From Best Friend To Boyfriend: Can It Work? 4 years ago 1

You’ve known him since childhood.

He went from the thorn in your side to the brother you never had. You can’t imagine what life would be like without him. You guys get along great. To him, you’re not one of the boys, but you are most definitely family. His mom loves you like a daughter and your mom loves him just the same.

One day, as he’s telling you about his usual sexcapades and groupie love, you feel the slightest pang of jealousy. It’s never happened to you before. Suddenly, he’s handsome, and has all of the qualities that you want in a man. It seems simple enough to take your chances by making a move. Consider this, unlike a stranger who’s just courting you, your best friend knows about ALL of your dirty laundry. In return, you know all of his. In the past, there were probably a few things about his behavior with women that you probably didn’t agree with. He probably wasn’t very fond of a few interactions you’ve had with men either.


Unlike a normal dating situation, your potential love affair will start with very deep roots. If this doesn’t work, you have the potential to lose more than just a lover. However, if things go well, the hard part is already done. You’re already in with his family and friends.

The communication between the two of you is expected to be easy because you were already friends. Here’s where things get sticky. You guys have never communicated as a couple.

Communicating as a couple would entail expectations far greater than that of friendship. It requires a different level of intimacy and selflessness. Being best friends will not necessarily mean that you’ll make the best couple. His past opinions about the opposite sex probably weren’t a factor before you two started getting busy. Now, you quite possibly overanalyze many of his statements and constantly hope that he’s as attracted to you as you are to him. The days of the accidental sleepovers are long gone. They’ll be replaced by normal thoughts of dating and the anxiety of what he may be thinking. The water may look a bit murky.

This may not be the case for everyone. Some things are best left unchanged. However, if you’re confident that a proposed union between you and your bestie will result in wedded bliss…go for it! Perhaps you silently wished for this moment, from the moment you guys met puberty. Maybe you’ve been tired of waiting for him to consider you a dating option.

There are a million stories of love staring directly in the face of friends. Circumstances make all the difference. If you believe wholeheartedly that the stars are aligned in your favor and you’re confident that you can bag your man…go for it. Men approach women everyday with similar expectations. The thought of being rejected by your bestie can be terrifying but if you’re ready to put your best foot forward and prepared for anything, you’ve already won by trying.


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