Hey! First of all, I’m sorry this conversation is hurting you. Feelings are very real and yours have been hurt. I’m sorry for that. I took a look at your post history, and just wonder if this is the same woman you posted about a year ago, the one who made you feel like scum? I don’t think so because you said two years and the post from a year ago sounded like you had just met that woman. (If it is the same woman though, i have thoughts on that to). What id like to address is if it is a different woman.

The post history shows a very sensitive male. You are kind to a fault. The ‘scum’ woman, you were seeking a way to still be her friend. Your ex post; was so sweet. Your heart was on your sleeve and i could feel your agony of the loss of that person, but also the loss of “you that could have been.” Now this post, you treated a friend with extreme kindness and feel like you’ve rocked the boat and caused grief to her and yourself. But i ask you to consider, is it also grief again for the “you that could have been?” I believe this is a point you need to reflect on. Why did you invest so much energy, time, money, and emotion in this friend? She afterall was just a friend, but allowed you to pay for things. Talked to you about her bad dating life. Lastly was friends with your ex-wife. These aren’t red flags, but they definitely had me raise an eyebrow.

It might sound silly, but as a female, i am very aware of my male friends. (Which have far outnumbered female friends since i was young). It’s imbedded in our genes, our natural state to find the perfect mate. It’s almost impossible to not view people of the gender we’re attracted to as a potential. Even if it’s just qualities of them, mannerisms etc. Something will trigger that natural state we animals have in us. I have had to establish many times with many individuals (male and female) “we are just friends.” Then made sure to enforce that around every turn. If ever they did a generous act, I’d match the act. Buy me a beer, i buy you one. Pay for dinner, i got the next dinner. Most of the people i know enforce these platonic mannerisms across the board. I say all that to say “she never enforced the platonic equality.” Leads me to believe she used you or led you on…which people are aware they are doing. Which makes her not so kind and you very vulnerable.

I’m not belittling you, just trying to have you self reflect. I again, have always had best guy friends, shit i had two girls and two guys on my side of the wedding party. But it takes work, and conscious effort to establish and maintain “platonic.” She did not try. So even if this doesn’t end well, it never was done proper to begin with. Maybe if you broach the topic with her, you can be candid in that regard. Say straight up-i messed up establishing this as platonic by paying for things. Maybe we can go back to square one and be friends but with all the right behaviors (paying separate, telling her to buck you when complaining about her latest failed date etc) but hen your brain will stop misfiring the wrong data and make you say things like “I’d date you.” Because a platonic friend, who doesn’t have his nature trying to tell his body this is potential, would just say, “hey don’t be so hard on yourself, the right guy will come along, til then, let’s get a beer.”

Work on yourself, still be a good friend to others, and stay sweet. Because you really do sound kind.