Friends of the opposite sex

I have a very good friend and coworker named Richard. He is the best salesman I’ve ever come across and I am lucky to have 3 accounts with him. I never worry about them leaving. In fact, they are the accounts consistently growing. So suffice it to say, he makes a lot of money and has a lot of connections.
Despite this, he is not your stereotypical sleazy salesman. He is one of the kindest, most genuine, big hearted people I have ever met. We have become very close as FRIENDS, over the last two years and will occasionally hang out. He is the kind of guy who does everything big. Forget about trying to pay, he absolutely refuses to even entertain the idea.
Once a month, because he works (telecommutes) in a premier suite in an expensive downtown hotel. He invited me and my best coworker out for dinner and drinks. He always says pack a bag and stay over. No worries about drinking and driving. His wife had a stroke a while back and needs 24/7 care so he usually leaves around midnight to go home. We have the suite until 4pm the next afternoon. Fully stocked, room service etc. Everything is top of the line.
Jason asked me what I was doing and I told him. Mind you, while we are probably more than casually involved at this point, we have no commitment. I do admit I have complicated feelings for him and our chemistry is above average but I have neither the time nor the inclination for more than we have right now. He knows this. We have talked about it. My dating profile on the site where I met him very clearly states “Would like to date casually but not looking for a relationship.”
Long story short, he thought it was impossible that I could stay over night in the penthouse suite of an expensive hotel with no strings attached. Basically saying I was either stupid or lying. To say I was pissed is an understatement! First of all, I’m not a naive school girl. This is not my first rodeo. Plus, I have known Richard personally and professionally for over two years. I have zero sexual attraction for him. Not to mention another mutual friend who is female was with us. I have pretty good intuition and am fairly skilled at reading people. Nothing bad was going to happen to me that night.
Then I thought, why am I even justifying this to him? So what if I was going to spend the night and fuck someone else? I am within my rights to do that or anything else I want. I am a single woman who doesn’t have to put up with suspicious, controlling accusations. If I wanted that, I would have stayed married! I love being on my own. I’m not saying I’ll never settle down but as for now? No way. I love my adventurous, unpredictable life. I’m completely honest about that and never pretend to want otherwise.
I know it’s been a big adjustment for Jason to go from being an every other weekend Dad to having full custody of his 12 year old daughter. It’s only been a little less than a year. She sounds like quite a handful on top of it all. So of course, he isn’t as free as he once was and it has put a serious damper on his social life. Trust me, this thing with me would probably have been a nonissue if he didn’t have his kid. This man could easily find a different woman everyday of the week if he wanted to but now most women want more than he can give. I don’t. In fact, it would seem I want less than he can give. Maybe that’s my appeal. I don’t know.
He kept texting me and expecting me to answer right away. Um, I am hanging out with friends. I can’t sit here sexting with you all night!! How rude it is to be texting while out to dinner or interacting with real live people? Wtf? I know he was drinking but he got stupider and more annoying as the night went on. Finally I told him, I’m done texting for the night and put my phone on DND. There were about 8 more texts when I checked in the morning. Drunk and stupid texts. This morning he apologized. He asked if I would talk on the phone (which I don’t like to do) but I did. Sigh. He is a real smooth talker. It’s what he does for a living. He makes me think of the pied piper. I accepted his apology but I’m wondering if this is just another example of the life long pattern i have of ignoring red flags. Once someone has won me over there isn’t much they can do to me turn off. This has led to disastrous consequences in the past. I’m not saying that is what is happening here but I just want to make sure it doesn’t happen again.
He is coming over tomorrow afternoon. I’m not sure what we are going to do yet but do I plan on going over some basic boundaries. Something I haven’t always been great about in the past. I work in a male dominated field, especially in the last two years. I have some very close male friends and in no way would I want to be with someone who was threatened by that or wanted me to only have female friends. Once again, if I wanted that, I would have stayed married.
I’ve been really looking forward to seeing Jason tomorrow. Despite wanting to keep everything casual, I do like him…

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