Dear B. Scott,

I’ve been dating this guy for a few months and things are going really great. I’ve met his friends, he’s introduced me to his family, and I basically spend all of my free time with him. We had a conversation a few days ago about taking our relationship to the next level and getting serious.

I’ve been through a few rough relationships and I’ve learned to keep my friends and the person I’m dating separate until I’m absolutely certain the new boy will be in my life for a while. I finally got to the point where I was ready to let him into more of my life and while I was having a conversation with my best friend about him, I showed my best friend his picture. I was completely shocked to find out the two of them have not only met before, but have hooked up in some capacity (no sex) months ago. My boyfriend’s often seen pictures of my best friend in my phone, but not once did he mention they knew each other. I asked him about it and he admitted that he met him once, but they both say they’re encounter meant absolutely nothing and they’re no longer in communication. If I had known this beforehand, I probably wouldn’t have gotten involved with him in the first place. But at this point our relationship is really good and I’m emotionally invested in him. 

Should I leave him alone for sake of keeping things not awkward or is it not that serious?

Dear love muffin,

It sounds like you’ve gotten yourself into a pretty awkward situation. But, it doesn’t have to stay that way.

You’ve already had a discussion with both parties involved and they have communicated to you that it meant nothing, they’re no longer in communication, and hopefully there’s no lingering feelings between them.

If this person is truly your best friend, they would want what was best for you and your happiness…which includes dating someone that they have a brief history with. I know you’re saying to yourself “out of all people in the world, why did life have to deal me a situation where a person that I care about interacted with my best friend?”, and yes I would be thinking the same thing…but sometimes you have to laugh about these types of coincidences.

It would be a whole different story if this was an ex-boyfriend or someone your best friend had an ongoing situation with…but it’s not. I would suggest that if you truly believe both parties involved, then as Whitley's therapist famously advised on A Different World, you should "relax, relate, and release."

You should also count your blessings, because as they say…things could always be worse. They could have slept together!


B. Scott

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