Would you meet/date an ex's best friend?

I dated a guy for about six weeks and I liked him a lot. But, there were some sketchballs stuff going on in his life and he was never around so I cut him loose. It was a very kind parting of the ways and we have chatted a few times since. It's been about six weeks or so since things ended. I am going to call him George, to make things easier.

Over the weekend, George's best friend (I am going to call him Jeff) liked me and sent me a message through an OLD site. I replied to the message and said, "I am pretty sure you don't know who I am, but I know you." Jeff replied, was interested to know how I knew him, and we started chatting. George never mentioned me to Jeff which doesn't really surprise me because I didn't date George very long. But, while we were dating, George mentioned Jeff a lot and told me quite a few things about him, none of which was bad or negative.

Another odd coincidence is that George wasn't my first brush with Jeff. I purchased a house a few months ago and my realtor referred me to Jeff's company for my home inspection and suggested that I specifically request Jeff. Jeff was busy and so Jeff's partner did my inspection. After George and I started dating, he saw something at my house for Jeff's company and told me that was Jeff was his best friend.

Anyway, I told Jeff that I dated George for about six weeks and that I had concerns. First, there could be a "bro code" issue. And, if we ended up dating, things could get awkward because we might possibly do things with George or see him. I said that I didn't want to create a problem between them that might affect their friendship. Jeff said that he wanted to meet me and that he'd "handle George."

Two days later, I got a text from George saying that Jeff told him that we matched online. In the text, he gave us his blessing (even though he said we don't need it), he said that we are both amazing people with a lot in common and would probably make a great couple, and he also said that "Jeff has a lot of time to treat you the way you deserve." He also said that I should take a chance on him because I might fall madly in love. And, that I should "focus on what I want instead of what's possibly in the way," meaning him. It was a nice text exchange but I am wondering if he still has some lingering feelings. It was almost too nice.

I am meeting Jeff tonight. It's so bizarre because he's picking me up at my house and I feel like I can already trust the guy to an extent because he is not a complete stranger to me. I just have so many concerns about this. I have never been in a situation like this and I don't want anyone to get hurt.

Thoughts, opinions and suggestions please.

Submitted April 24, 2019 at 06:14PM

I dated a guy for about six weeks and I liked him a lot. But, there were some sketchballs stuff going on in his life and he was never around so I cut him loose. It was a very kind parting of the ways and we have chatted a few times since. It's been about six weeks or so since things ended. I am going to call him George, to make things easier.Over the weekend, George's best friend (I am going to call him Jeff) liked me and sent me a message through an OLD site. I replied to the message and said, "I am pretty sure you don't know who I am, but I know you." Jeff replied, was interested to know how I knew him, and we started chatting. George never mentioned me to Jeff which doesn't really surprise me because I didn't date George very long. But, while we were dating, George mentioned Jeff a lot and told me quite a few things about him, none of which was bad or negative.Another odd coincidence is that George wasn't my first brush with Jeff. I purchased a house a few months ago and my realtor referred me to Jeff's company for my home inspection and suggested that I specifically request Jeff. Jeff was busy and so Jeff's partner did my inspection. After George and I started dating, he saw something at my house for Jeff's company and told me that was Jeff was his best friend.Anyway, I told Jeff that I dated George for about six weeks and that I had concerns. First, there could be a "bro code" issue. And, if we ended up dating, things could get awkward because we might possibly do things with George or see him. I said that I didn't want to create a problem between them that might affect their friendship. Jeff said that he wanted to meet me and that he'd "handle George."Two days later, I got a text from George saying that Jeff told him that we matched online. In the text, he gave us his blessing (even though he said we don't need it), he said that we are both amazing people with a lot in common and would probably make a great couple, and he also said that "Jeff has a lot of time to treat you the way you deserve." He also said that I should take a chance on him because I might fall madly in love. And, that I should "focus on what I want instead of what's possibly in the way," meaning him. It was a nice text exchange but I am wondering if he still has some lingering feelings. It was almost too nice.I am meeting Jeff tonight. It's so bizarre because he's picking me up at my house and I feel like I can already trust the guy to an extent because he is not a complete stranger to me. I just have so many concerns about this. I have never been in a situation like this and I don't want anyone to get hurt.Thoughts, opinions and suggestions please.