My very long story. Advice requested. I already know I'm dumb.

[BarneyMosby]

So I've never posted to an advice forum before, but I felt I needed to either get reassured or be put in my place by some people who were neither my family, friends, nor anyone involved in this story. It is kind of long, but I'll post cliffs at the end for the TL/DR folks.

Begin Novel (names are changed to protect against internet detectives):

I need to start with a little back-story. Soon after college I met my future ex wife. Let’s call her Lilith. We dated for several years, through a long spell of long distance relationship, and got married. Over that time this woman drained me emotionally and financially. It really was miserable. But we ended it and left it as friends. Problem was, she was very sick and really couldn't support herself, and I had the ability to, so I made sure she was taken care of until she found someone else, but then she got real sick (Big C) and new guy couldn't afford to pay for everything, so I made them a loan (stupid, but I didn't want her to die or anything).

My continued contact with Lilith pretty much ruined any relationship I tried to have over the next couple of years; I thought it was always because the person I was with didn't understand that it was only a financial relationship. It destroyed a pretty decent relationship I had with a girl named Emma, because I made the mistake of asking Lilith for some advice about it. Emma and I broke up and I moved away, but we stayed in contact with random emails over the following months just to check in on each other and remain friends.

At this point I should mention during all this time I had been moving around for work. Lilith lived in State 1, Emma in state 2, and I live in State 3 right now. After about a year in State 3, I met Joan. I fell in love almost immediately. Joan was everything I could want in a girl, beautiful, wicked smart, fun, athletic, played video games, loved to eat, great family, not a leech like Lilith, and not flighty and possibly untrustworthy like Emma.

The relationship was going great, until I tried to do something that I really regret. Since I still needed to have that contact with Lilith because of the loan, I decided to introduce Lilith and Joan to show Joan she had nothing to worry about since Lilith was re-married and everything was just friendly. Wow, I still kick myself for that. It all seemed to go well, but that was the beginning of the end.

Another month or so goes by and everything fell apart in a perfect storm. Joan was mad at me for something and it escalated into a big argument, Lilith was pressuring me for more money and offering her unsolicited (I learned my lesson from the Emma advice) advice about Joan. Lilith actually contacted Joan somehow and started berating her and saying a lot of mean things. I told Lilith off pretty harsh and told her I was going to cut her off and out of my life, I didn't care how much money she and her husband owed me, it would be worth it to get her out of my life. Joan somehow gets it in her head that I didn't defend her in the situation and that I chose Lilith over her somehow. During this time Emma's dad passes and she contacts me as a shoulder to cry on. Being the sympathetic idiot I am, I answered the call and after talking her down she asked me how I was doing and I stupidly told her about the situation and she gave me advice, stick with Joan if I loved her like I said I did. I told Emma that I didn't want to make the same mistakes twice so she and I couldn't be in contact while I was with Joan anymore.

Here is the rub; I am honest to a fault. Whether it hurts me or the other person I am always honest. I told Joan about the call from Emma. She got pissed and finished breaking up with me. We went our separate ways for a few weeks.

Now I have to say something about State #3. The place where I live is small. Maybe a couple hundred thousand people, but the young single scene is small enough that everybody is 1 degree of separation from everybody else at the most. No exaggeration. You run into the same people out and about every weekend. Well Joan continued to go to my favorite after work watering hole all the time after we broke up. A couple weeks after we broke up she obviously started dating this guy, let’s call him Rush, cause he was a fat, ugly, radio talk show host who thought he was Rush Limbaugh, and he has the personality to boot. I flipped off the deep end.

This would be my first lesson in just how small this town was. When out with my friends, I would bitch to them about her and Rush, who I hated even before they started dating because he really is a bad person. I did leave her a nasty voice mail, I wasn't yelling, but I was pretty much just going off about how I couldn't believe she started dating somebody 2 weeks after a day in which we had supposedly loved each other. In my 33 years at this point I had never had a "rebound" so the concept was both foreign and seemed ridiculous to me.

Well after a while she finally realized what a scumbag Rush was (she told me later he actually made fun of one of her best friends who has a neurological tick caused by an illness she had right to her friend's face). I gave it some time and I contacted her to apologize for my behavior. We decided to get back together. I was the happiest I could be, I felt I had learned from my mistakes (while we were broken up I cut Lilith off, ate the $25k she owed me and called it a decent cost for having her completely out of my life).

This time around there would be nothing standing in our way. Except for the fact that she never considered us back together. Sure we did everything two people in a relationship do, including practically living together, but according to her we were never in a relationship, because about 5 months later, one day she calls me and says we shouldn't hang out anymore. Sure we had been arguing a bit, mostly about stupid ideological stuff like politics or the economy, and mostly because she took my want to have a well thought out discussion about a topic as a want to argue. So we weren't perfect, but those arguments were rare. Not bad enough to cut everything off with a knife.

So I found out a week later that she had met somebody else the week before she cut us off. She swears she never physically cheated on me, and I believe her because I was basically living with her right up till the end, and we were not "in a relationship" anyways.

This time I didn't freak out, but I was depressed. And I needed closure. I actually came on here and had a post all typed up to this point looking for advice. Never posted it though.

Fast forward another 2 months or so and I contacted her. I told her I wanted closure and I would like us to be friends. She agreed. (Come to find out I had timed my contact perfectly with the day her and Coked out Bob Vila broke up) Then she reneged for some reason a week later.

The next few months are kind of a blur, I dated a few people, not seriously, stayed out of contact with her until some point, which I can't remember I contacted her and we decided to hang out. Well we actually became great friends. We both were kind of seeing other people, we gave each other advice, and it was kind of nice. I loved her to death still, but I was pretty content with the way things were going. Then we both got single again. I know she was hanging out with Rush again, but I was told it was mainly because she had met two new girlfriends who were part of that crew. Hell I even had friends in that crew, that is how small this town is. One of those new girlfriends is important to the story; let’s call her Pepper. Joan thought Pepper and I would be great for each other, and told both of us that she would introduce us.

Time went by, Joan and I were hanging out almost every day, but she never introduced me to Pepper. In fact supposedly Pepper was acting in a way that I guess was not pleasing Joan too much and Rush did something extremely bad again, so Joan said she didn't want to hang out with that entire group anymore. She and I started hanging out every day, and eventually things got romantic again. Again it was great; she told me that I had changed so much from the person she first met that had I been this guy all along we probably would be married by now. This pretty much made my day, week, year, life.

It was a great couple of months, but then Joan got an awesome promotion at work that forced her to move to another state (State 4). I was crushed. A month or so before she moved we made plans for me to help her drive up there with her move, and for me to come up in another week to help her finish unpacking and explore her new city. She said she really wasn't wanting a long distance relationship but was willing to take things slow.

Well I could tell things were about to go bad when a few days before her move she didn't remember me buying the flight to come see her the following week (when we hung out she got a lot more drunk than I thought she was getting since we were at home and not ordering drinks, just sitting around). She also didn't remember a bunch of other stuff. Well the day of the move came, and I'm not going to get into it much, but I got in an accident with the moving truck right after picking it up. So it threw her whole move into chaos. I offered pay for the last minute price difference in a smaller truck but she wasn't having it, she opted to pay for pros to come and drive the stuff, and left me at home, cancelling my flight back.

Then after she had been up there a couple days she called and told me to cancel my flight for the following weekend. And that she just wanted to be friends and was no longer willing to even take things slow. Then a few days later she said we shouldn't even communicate until I was over her. I've gotten that text before. That means she met someone up there. So I said fine, whatever.

I didn't plan to date anybody for a while. I had no interest in it. I did go out and party, but I purposefully went home alone. I didn't want anything to do with anybody.

Now here is where my reason for writing this novel finally comes out. This is what has happened in the last 10 days or so, starting about 10 days or so after Joan said we should not communicate. So it turns out another set of friends of mine (not the ones in Rush's crew) I hadn't seen in a month or two, because of spending all my time with Joan, became friends with Pepper. I was out with them one night and Pepper came out. I was pretty sure that she was the same girl, but not 100% positive at the time. We hit it off as Joan had suspected previously.

I found out the next day, via the evilness that is Facebook, that she was the Pepper that had been friends with Joan at one point. At this point I was under the impression that they were not friends anymore and hadn't talked in the last month or so (and had only known each other for 4-5 weeks before that) and I confirmed that with Pepper. Pepper and I happen to be big fans of the same non-local NFL team, so we decided to go check out the game the next night. It was not supposed to be a date. Well it turned into one. I hadn't hit it off this well with anybody else in my life except for Lilith and Joan.

So we hang out a few times and then go out one night and run into the Rush crew, minus Rush. Well a bunch of them decided to take it upon themselves to text and call Joan and let her know what was up. Joan blocked us both on Facebook, but supposedly told those people "she was happy for us and that she was dating some new guy where she lived," because those people admitted to talking to Joan and told us that.

So everything is going great with Pepper, but stupid me, I decided to email Joan and tell her that I understood why she blocked me, and that I hadn't gone after Pepper, it just worked out like that, and that I was happy she found someone new and that I hoped he made her happy. I also told her I didn't expect or need a response. She called me on my work phone an hour or so later. She said that she wasn't angry at me, but felt like I slapped her in the face for dating her friend and she was hurt and she would never do that to me. I told her that I was told they hadn't even talked in a month and that they were not even that great of friends in the first place. Also I told her that Pepper said she had been in State 4 two weeks earlier and she texted Joan to get together but Joan ignored her. Joan said that was all lies, she did respond, and she also loaned Pepper money right before she left town.

She also said that she had had an opportunity with one of my friends after we broke up but she didn't take it. Let’s call that friend Bilbo. My guess is there is more reason than he was a friend of mine for why she didn't date Bilbo. My guess is if my other friend Gerardbutleryoungrusselcrowe would have been interested she might have taken the chance.

She also went on to tell me some pretty disturbing stories about Pepper. Stories of both promiscuity and morally bankrupt behavior. The stuff was a little bit too strange to have been made up. She also told me Pepper didn't have a job (which I knew she was recently let go from a position). Then she told me the thing that worries me the most, she guaranteed that Pepper would become a Lilith II. I can forgive someone for their past, no problem, but I cannot live with another Lilith. I wouldn't survive it.

Side note: Pepper also told me that when she met Joan that Joan was dating Rush. I was like that can't be, Joan and Rush dated a year before you moved to town. So maybe Joan lied to me about that? Come to think of it the timing between when she told me Rush had been a jackass again and when she and I became romantic again couldn't have been but days apart.

The thing is I really like Pepper. I know it’s been a very very short time, but we both like each other a lot, and she hasn't given me any reason, that she knows about, to break things off.

Cliffs:
- Ex wife Lilith was crazy, controlling, emotionally abusive, financially draining
- Ex wife Lilith damaged several relationships I've had since
- Was extremely in love with Joan (maybe still am a bit) on and off again relationship, she crushed me twice.
- Joan leaves town, I start dating her quasi-friend Pepper a little under a month later
- Joan blocks us both online, I apologize via email
- Joan contacts me by phone and goes on to say all sorts of stuff about Pepper that makes me pause

[BarneyMosby]

Questions:
- I know I'm a dumbass when it comes to relationships (which sucks because otherwise I'm very intelligent) but was I wrong to date Pepper at all?
- Suggestions about what to do with Pepper. I do really like her, but I am worried that she maybe be putting on a front (somebody is lying about how recent they were in contact with each other, they can't both be true) and I can't handle another Lilith.
- I obviously can't confront Pepper about anything, can I?

Own observations:
- I do still care about Joan, but I obviously do stupid stuff when I am hurt. I wanted to marry Joan, I would have thrown the world off its orbit if she told me she was a little warm.
- If Pepper is not lying, despite the stuff in her past, I think we have a good chance.
- I need to get the f-bomb out of this messed up town.

[Valixy]

Why on Earth do you allow your ex-es to comment on your new relationships and let that influence you? Women dislike this very much as you could have noticed by now.

Joan is not interested in you anymore, she had several opportunities and never found you were enough for her. Stop emailing her, transporting her furniture, doing any kind of favours for her. She's a big girl and she can look after herself. She doesn't love you but likes to keep you in the background in case anything else fails.

Pepper might be a rebound for you but you two get on well. Even Joan predicted it but was too selfish to introduce you to each other properly. So, Pepper has a past and Joan got pretty low to comment on it (or make up part of it ?) and all this while she hasn't been capable of respecting the relationship with you and the other guys she's been seeing in the last years (!) I think that you should really ignore Joan and have the dignity to get to know Pepper on your own. Just because she doesn't have a job at the moment it doesn't mean that she couldn't get one or that she is a worthless person.

On a side note, you also have a past. If Pepper knew about the habit you have of ruining your relationships because you keep being somehow dependent on your ex-es' opinions, you wouldn't look very good either.

[BarneyMosby]

Why on Earth do you allow your ex-es to comment on your new relationships and let that influence you? Women dislike this very much as you could have noticed by now.

Joan is not interested in you anymore, she had several opportunities and never found you were enough for her. Stop emailing her, transporting her furniture, doing her any kind of favours. She's a big girl and she can look after herself. She doesn't love you but likes to keep you in the background in case anything else fails.

Pepper might be a rebound for you but you two get on well. Even Joan predicted it but was too selfish to introduce you to each other properly. So, Pepper has a past and Joan got pretty low to comment on it (or make up part of it ?) and all this while she hasn't been capable of respecting the relationship with you and the other guys she's been seeing in the last years (!) I think that you should really ignore Joan and have the dignity to get to know Pepper on your own. Just because she doesn't have a job it doesn't mean that she couldn't get one or that she is worthless person.

On a side note, you also have a past. If Pepper knew about the habit you have of ruining your relationships because you keep being somehow dependent on your ex-es' opinions, you wouldn't look very good either.

Thank you for the reply! Oh yeah, I definitely noticed.

This is basically the conclusion I've come to. Pepper's past doesn't really bother me all that much, more so I was concerned that she may have been lying to me since she said she hadn't talked to Joan in a month, yet Joan said she loaned Pepper money. The whole she doesn't have a job thing really doesn't bother me right now, especially because the girl does seem to have a lot of ambition, which I like.

I think I'm going to take it slower with Pepper, and I'm definitely going to ignore Joan, though she already said that she never wanted to see me or talk to me again anyways. It kind of sucks, I felt stronger about her than about anybody else in my life, even Lilith before things went bad. And it hurt worse than any other relationship because I've never dealt with anyone who could move on so quickly. I am trying to do the same myself right now I realize, and it is not easy. It is what it is though.

Ironic side note, Joan and Lilith, in real life, have the same name, even spelled the same.