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[Read: 20 unmistakable signs your friend is crushing on you too] The cons of dating your best friend Before you take the plunge and pursue a romantic relationship with your best friend, take a moment to consider the following drawbacks. It’s always the number one concern when anyone considers dating a friend: what if it doesn’t last?

If you break up, you might have to accept that your friendship might be lost forever.

The good news about dating your best friend is that the awkwardness has already been dealt with, and you can simply enjoy the excitement of taking your relationship to the next level. Not only will you already have a solid emotional bond, but you most likely have a shared history.

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Trust me, there already is a relationship, and something significant is about to happen to it.

If you’re hoping to go the distance with your best friend, you’ll already know if your future aspirations align, which will allow you to prepare for the possible path ahead. There’s nothing more awkward – or in some cases, upsetting – than discussing your partner’s dating history.

But, you’ve most likely had that discussion with your best friend without the implications of being in a relationship. Perhaps they’ve cheated in the past or have had various relationship issues.

Here is the basic scenario: What if you have been long-time friends with a girl for three years and recently you started seeing her in a new light?

We already hang out either with a group or alone pretty often. And how do I find out how she feels without making it awkward?

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