I’m trying to make this as vague as possible. Would any of you guys ever talk to a guy that has a history of playing girls even if it seems like he really likes you and his feelings are genuine. People that know him are surprised to see him act the way he does around me and i’ve liked him for a long time. 3 years to be exact. We are close friends for context.

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#1

My sister's best friend started dating a guy who had been through at least 3 relationships in 6 months as they have now been together for almost 10 years.

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#2

Tread these waters veeery carefully. I think I have a method, but it might be a bit challenging if you are of opposite sexes, you'll see why in a moment.

You say you are close friends, just how close? Like, "he knows all my secrets" close? "We love each other as friends" close? "I could hug him and he wouldn't think its sexual" close?

If you answered yes to that last one, then congrats! You are in a deep platonic relationship! This makes it a lot easier to test out his romantic side without directly putting yourself in danger of being heartbroken.

Then, just get into asking him about romantic preferences, like a concerned friend looking to get her platonic soulmate a romantic partner. Once you get any answers you're looking for, you could choose to move forward and pursue a relationship.

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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

This helped more than you know. I love him as a person and we do tell each other that we love each other regularly.

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#3

It's hard to say without specifics. Was he just dating girls, or was he having relationships with them? And was he honest? If it's something he used to do, or he was just dating and not in relationshipa with them, I'd say give them a chance, but remain cautious until you know for sure. If it's recent behavior, and if he wasn't honest, even though you like them, I'd steer clear. People do change, but if they are showing you over and over who they are, I'd pay attention.

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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

he hasn’t dated a girl in 2 years. All he does is flirt and talk like he has feelings for them or just extra friendly. He seems to be honest with me so i don’t know.

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#4

When it comes to knowing whether or not your heart is safe with him, the question is not, “am I different than other girls?” The questions are, Has he grown as a person and taken accountability for his past behavior? Does he have remorse for how he has treated other women? Was his treatment of women just a matter of immaturity or is it deeper than that (I.e. learned behavior, cultural, narcissistic type behavior etc.)? What does a healthy relationship look like to him and does it align with your view? In your friendship, has he demonstrated trust? Respect? Healthy communication? I would open a conversation with him and get some answers before allowing your heart to be vulnerable around him.

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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

This definitely helped. We had a conversation similar to the one you’re suggesting and we decided that during the summer we can talk and get to know each other in a deeper way and possibly date when the summer is over and school starts.

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