It's hard to summarize my history with this girl since I've known her for about 30 years, but here goes. I'm reconstructing this timeline as best as I can from memory, text messages, and her voice message just to give you a lot of backstory and summary of events over about the past few years. It helps me get my thoughts together if I type them out, and I'm genuinely curious to hear what people think (both the good and the bad).

Just to be clear, I've always viewed this woman as a friend, and I've never pursued her or had feelings for her as anything other than friends until about the past year for reasons to be revealed below. I am realistic and realize I am obviously in the friend zone. Over the past year, there has been some very light flirting from her. As a result, I occasionally started spending more time now and again hanging out with her at her insistence and request.

I've known her since the 1990s when I used to hang out with her brother and her all the time in high school. Her brother got hooked on drugs and eventually died a few years back. I know this has affected her a lot obviously as we've talked about it too. He was a good friend of mine until he got hooked hard on drugs, after which we started to lose touch. I would still see him occasionally when I would come visit her as a friend.

It was really sad to see what happened to him. I've had my own struggles with sobriety (also drugs), but I managed to graduate from college and obtained an advanced degree to become a working professional. For a long time, I guess you could call me a functioning addict who could hold a job and make decent money until it started to catch up to me as I got older and didn't have the energy I did when I was younger to maintain that kind of lifestyle.

She also has a history of addiction and drug abuse, but she managed to earn her masters degree and now teaches at a college.

During Covid, I hit some rough times while still managing to survive and not end up homeless. I actually moved to another state for about 2 years and 3 months due to the cost of living in California going up like crazy due to inflation. Those 2 years and 3 months outside of California ended up being one of the best things that could happen to me.

Since I didn't know anyone out there, I couldn't readily score drugs like I could in California. I know I could find it if I looked hard enough, but I used the time to get off hard drugs. I didn't go to NA or anything like that. I just kept working remotely, slept a lot in my free time, and hung out with a friend from California who ended up moving out to the same state as me.

To make a long story short, I started working remotely with someone in my field who lives in California. It started out slow, but we started to get more and more business to the point where this person told me it was time for me to move back to California since we were getting more and more busy.

Ok, back to the girl. She has not had the best experience with past boyfriends. One of her former boyfriends used to beat her up almost on a daily basis. One time she came into her room to find him standing in her closet holding a knife. He had cut up all of her clothes. He was that kind of psycho. She has a daughter with him. She eventually had him locked up. They were on and off again, but she finally moved on as far as I know.

About a year ago, when all of that was going on, I casually invited her to come visit me if she wanted to get away from the craziness for a while. I was just doing it as a friendly gesture and honestly wasn't expecting her to say yes. Well, she asked her mom who put her on the next plane out to visit me since her mom had it with that ex boyfriend. I've always gotten along well with her mom who seems to like me.

She visited for about 4 nights, and I showed her around to a lot of different places. I didn't make any moves on her, because she's a good friend and I didn't want to hit on her when she just got done dealing with her psycho ex. I also didn't want to make it awkward for her since she was crashing in my room for those 4 nights. But she would flirt with me a bit. Nothing major.

Honestly, while I've always thought she was cute, I didn't have strong feelings for her since we've always just been friends. And I get that I'm in the friend zone.

But here's the weird part. When she first arrived after I picked her up from the airport, one of the first things she told me when we got back to my room and were alone was that she asked her daughter how she felt about dating me. Her daughter told her she was in favor of her mom dating me since her daughter thinks I'm nice.

She also told me she did a tarot reading about us before she came out to visit me. I told her I'm a bit superstitious about that kind of thing and didn't want to know what the tarot reading told her. I did say I'm interested in paranormal stuff and hearing other people's stories about things like ouija boards, but I would never use a ouija board. She agreed about not using ouija boards, but she's into tarot cards. Whatever. Doesn't bother me.

When she told me these things, I kind of laughed and played it very cool. Again, I've known this woman for about 30 years as a friend. Thus, even though I've always thought she was cute, I just don't know if she's interested or is just using me for attention and a distraction from her problems with boyfriends. And even if she is interested in me, I honestly don't know how to make that transition out of the friendzone without coming across as a creep unless she made the first move or gave me some very obvious physical hints. For those reasons, I've played it cool with no real expectations of our time spent together and just assume I'm in the friendzone as always.

We had a fun four days. It was strictly platonic except for some mild flirting. She would ask a waiter to take our picture. She would hold onto my arm a few times. She would tease me by asking if it was okay to grab me before she would grab my arm. Nothing major. She sometimes uses a cane to walk since her balance is not always the greatest due to a medical condition. But she is able to walk, work out, etc.

Eventually, she returned home, and I went about my business as well. I happened to be visiting her town for one night back in January of this year and let her know I would be in town. She invited me to come hang out at her place with her new boyfriend (not the psycho ex). She lives with her mom and her daughter.

I said sure. I didn't make a big deal of it since up to this point we're just friends, and we're still just friends. I'm realistic about that. I did think it was odd that her boyfriend would be cool with that, but I figured he must be a cool dude who doesn't get jealous or something. Well, I go over to her place, and it's just me and her hanging out in her bedroom. Her daughter would come in to chat a bit too.

Then I realize that her boyfriend is there, but he's in the shower. Her bathroom opens up to her bedroom. It's a small bathroom with a toilet and shower. I didn't see him when she would open the door to talk to him, so he must've been sitting/standing in the shower. I was there for something like 3 hours and not once did he come out to meet me or talk to me.

Even if he did, I wasn't going to be jealous or hostile towards him. I wasn't tripping since at the time I was still living in another state, and she wasn't my girlfriend or anything.

Fast forward to early May of this year, and I finally have the opportunity to move back close to where she's living (our hometown where we both grew up) due to my business finally starting to take off. I texted her just to give her the heads up. She responded and said she can't wait to hang out. Etc.

In June, my friend was having a private sushi dinner birthday at a sushi place we both frequent. He's good friends with the owner. It was $200 per person (not including tip or alcohol). Since I appreciated the fact that this girl flew all the way to visit me in an other state, I invited her to come with me and paid for her dinner. I really just wanted to show her I appreciated her coming to visit and again didn't hit on her or anything.

I also did this because I felt bad that she had to spend money buying some bedding when she came out to visit, because I'm a bachelor who wasn't honestly prepared to have a guest. So she bought me some sheets, blanket, etc. This was due to me being low on funds during the first two days of her visit, but then a new client came through on payment and I was able to treat her a bit for the remaining two days.

We just had a good time at the sushi dinner and hanging out. Afterwards, I drove her home and dropped her off. After I dropped her off, she would text me about how she liked the dinner. I sent her some pictures of the dinner since she asked me to take pictures on my phone so she could show her daughter.

She then texted something like "Not to be rude, but how much was that?" So I told her, and I assured her not to worry about it and that I appreciate her coming to visit me. I told her I felt bad about that and wanted to treat her to something nice.

Again, I was just being a friend and not expecting anything back and still don't. I definitely would not have done this with any other girl I barely knew. She also mentioned something at the dinner about her boyfriend who I assumed was the weirdo who wouldn't come out of the bathroom back in January.

After that sushi dinner, we lost touch for about a month. At the time, I felt like I just paid back my friend and was not expecting anything else. About a month went by, and then I happened to be talking to our mutual male friend who was visiting his parents up in northern California. He wanted her and I to come visit him.

I told him I think she has a boyfriend and that I wasn't sure if she would want to go. He must've called her and told her what I said (I assume), because she called me that same night about an hour or so later. It was late at night when she called.

She told me she was totally down to go visit him, but she wouldn't really be free to do so until some time in August since she was teaching summer school. I said that sounded cool and that I will see if I have time available since I'm also busy with work. She then said she wanted to hang out and spend more time together before that, so I agreed. I'm always friendly with her and let her know I'm down to hang out, but I don't fully chase or pursue since I know she has or had a boyfriend.

That was in July, and we lost touch for a few more weeks since I was busy and I assume she was busy too. Then she calls me out of the blue to ask what I'm doing. I said not much other than work. We agree to go hang out somewhere. Finally, around mid-August, we made plans to go do something. Originally, she was going to come to my place, and I would drive us to get food.

She later asked if I could pick her up instead, and I said sure. I go to pick her up. I texted her when I got there and let her know I was in the parking lot in my car and not to rush. She always takes forever to get ready since she's a girl.

There was also some guy working on his car parked in front of her driveway. I assumed that was her boyfriend, so I just stayed in my car where I don't think he saw me. Eventually he leaves in a car with another girl. I'm sitting there for like an hour, so I texted her just to see if she's almost ready. She replied something like "Almost. It's been a crazy day." Finally, she invites me into the house to say hi to her mom and daughter while I wait, so I go do that.

She's finally ready, so we get in my car, and I drive us up the coast. I didn't pry at all or ask about the boyfriend. She volunteered that they had broken up recently, and she was having him pick up some of his things. They had gotten into a huge argument. She said he yelled at her or hit her or something (not that day but I think a day or so earlier), but he never does that when other people are around. She explained she called her female friend to come pick him up since she knew he wouldn't do any of that with her around.

I always tell her not to hesitate to call the police if anyone threatens her or puts hands on her. Her first ex boyfriend (the psycho) told her she was a snitch if she told the cops he hit her. I told her that's b.s. and that it's not snitching if a full grown man is beating up a tiny woman like her.

Anyway, we're driving up the coast headed to some beach towns. I asked her where she wanted to go eat and suggested a few places. She said she liked this fancy restaurant with an ocean view, and she also suggested a dive bar near the beach. She told me the dive bar would be cheaper, but I told her let's go to the more fancy place since I had actually never been there despite growing up in the area.

I should also mention that she was all dolled up and wearing a dress. She looked better than I had ever seen her before. I know she was probably dressed that way to get attention and to make herself feel better, but, hey, I'm not going to complain. But she never flirted with anyone else when we were hanging out, and she was always focused on hanging out with me and talking to me. Since she was so dressed up, I was happy to take her to the more fancy place. She never asks me to spend money on her and usually opts for cheaper options, but I don't mind treating her since I've been staying busy and business is going well.

We ended up having a drink each and shared a cheese and meat board. I then drove her back and dropped her off. I parked right in front of her front door and got out to open her door and give her a hug. As I was hugging her, I happened to look up and made eye contact with some guy's head peering out from behind the front door. I made direct eye contact with him as I was hugging her and didn't look away. She goes inside, and I call it a night and head home.

Since her boyfriend was obviously still around, I shrugged it off and figured I wouldn't hear from her for a while if at all. The next day, I see a call coming from her, so I answer. It's some dude. He was saying something about wanting to meet me. I asked who he was, and he gave his name. He said I've been taking out his girl and wanted to meet me. He said something like "What kind of man does that?" Keep in mind I'm almost positive this is the same boyfriend who wouldn't come out of her bathroom in January, but I haven't confirmed that to be true yet. He didn't threaten me, but his tone was threatening/hostile.

I told him I've known her longer than him, that I don't owe him ****, don't have time for this, and was not going to meet him. He kept saying, "Wow!.... wow!..." I could tell he was winding up to say more, but I just hung up on him.

I got busy with calls for work, but I saw her number calling again. It went to voice mail. When I finally was free about 40 minutes later, I checked the voice mail and it was her. Here is what she said in the voice message I still have on my phone:

"Hey [my name], it's [her name]. I'm sorry about that. [Her boyfriend] uh... we just had a conversation, and he raised his voice at me. Anyways, the cops came by and arrested him actually since he had a warrant. But anyway, I got my phone back. I apologize for the drama. Give me a call when you can. I apologize. I know I suck. Alright, I'll talk to you soon. Bye."

I called her back and let her know I was busy on the other line with a client, which is why I missed her call. I told her not to worry about it, and I told her exactly what happened (exactly as I explained it above.) She kind of chuckled and seemed to find it amusing.

She said she was having him come over to pick up his clothes, and she said he hit her, but then she changed it to say he raised his voice at her. There just happened to be a cop nearby, so she flagged the cop down who arrested him since he had a warrant. I didn't ask what the warrant was for, and I don't care to be honest.

The next night, I'm hanging out at my friend's place, and she texts me around 9:00 p.m. to ask, "So when are we going to the gym?" We had talked for a while about going to the gym together like we did when she came out to visit me out of state.

I texted back that I was pretty busy early in the week, so I suggested Friday or Saturday. I also asked her if she was interested in hiking this trail that goes out to the beach. She said she was down if it wasn't too hot outside. I said if it's too hot, we can go to the gym instead.

She replies, "No I'd like to do both." So we start texting about new trails she's interested in checking out. Etc.

We finally agree that I would hit her up on Wednesday after I was done with work. This week would end up being the most time we spent together since she came out to visit me out of state about a year ago.

On Tuesday, I followed up with her to see when she wanted to go hiking or to the gym only because she originally was the one to hit me up about doing these things. We both agreed that we were tired, so we were going to play it by ear. We were definitely going to hang out, but we weren't sure when yet.

That same Tuesday, she texts me later in the day asking for a favor. I have a computer with a printer, so she asked if she could come over and work on her syllabus or something for the classes she teaches. However, she ended up getting stuck checking on her daughter, so we agreed it was too late and we both needed sleep since we both worked the next day.

Wednesday rolls around, and she said she's too tired to go to the gym due to work (she has early class hours). No biggie. I just found it funny/amusing since she's the one who had made a big deal about wanting to go to the gym and go hiking. Even though she didn't want to go to the gym, she asked me what I was up to. I told her not much other than sending off some emails for work and asked if she wanted to go do something.

Long story short, we ended up going to see a movie that same Wednesday, and we brought her daughter since she wanted to see it too. So we saw that movie, and I dropped them both off at home afterwards.

Also, sometime that same week, she invited me to go with her to one of those pitch meetings where you get a free dinner if you sit and listen to their pitch. It was some annuity investment firm. That dinner was on Thursday of that same week. She didn't really want to go, but her mom was pushing her to go, so she invited me and said it should be a good time if I'm there and that she values my opinion. Etc.

So we went to that dinner, and they had us fill out a form. On the form, it asks for your spouse's name. She looked at me and said she was putting me down as her spouse. I laughed and smiled and said I would put her down as mine. I'm pretty sure she was just teasing/messing with me, but it made me laugh.

Also, I found out my friend and his girlfriend were coming to our area on Friday of that same week. This girl I've been hanging out has met him before, so I invited her to come along with us. The four of us all hung out, got a drink, got dinner, etc. She said she had a really good time, and I dropped her off at home afterwards.

The next morning, I texted her around 1 p.m. and said I got up super early, got some coffee, and then passed out. She said she kind of did the same thing, so she found that funny. She said again she had a lot of fun last night.

Then on Sunday she hit me up asking me to come over and use my computer again, and I said sure. She was busy and didn't come by until about 9 p.m. Again, she was dressed up in a dress and looked nice. I helped her out with her syllabus (mostly typing what she dictated since I'm better at typing than her lol). We ended up not finishing until about 12:05 a.m. We hugged a little longer than usual this time. I asked her if she wanted to go hiking or to the gym later that week, and she said maybe.

I asked her if she was ok to drive since we were both tired, and she said she was fine. She said she'll text me when she got home, which she did and thanked me for my help. I said no problem and thanked her for coming over.

Two days later (Wednesday), I texted her in the afternoon and said I was almost done with work for the day and asked if she wanted to hiking or to the gym sometime that week. After about 20 minutes, I see the read receipt that she saw the text. No response.

Three days later (Saturday), I texted her again and said I hope her weekend is going ok. I said hit me up if she wants to go to the gym, get food, etc. Same thing. She or someone read the text. But no response. It is now Thursday (5 days since my last text) and still no response.

Alright, now here's where I'm not sure what to do and what I've concluded:

1. She may not be interested and is ghosting me. If that's what it is, it is what it is.

2. Her boyfriend may be out of jail, and maybe he's not letting her respond to my texts since they got back together.

3. She may just be tired from spending so much time going out with me and needs a break.

4. She may be busy with teaching since her classes are just a few weeks into the fall semester.

5. She may be busy with her daughter, family, and other personal things.

I think those are the most obvious reasons, and it may be a combination of some of those things. So I am assuming she is either not interested, only sees me as a friend, and is possibly back with her boyfriend or with some other guy.

While it caught me off guard a bit that she would go silent on me so suddenly like that, I'm not going to text her or speak to her until I hear from her. Not because I'm mad at her or anything. I just figure she wants her space for whatever reason, so I'm getting the hint and leaving her alone.

All these times I took her out, I wouldn't let her pay. I in no way think she "owes me" or anything like that. I really liked hanging out with her even if nothing comes of it. Everything I've read online and what my friend told me says don't text her any more until she reinitiates contact.

I thought we left things on a good note, so I don't think she's mad at me. But maybe she finally realized that I was starting to like her, so she's backing off if she's not interested.

This isn't my first rodeo, and I've had similar experiences with other girls I've dated albeit none that I knew as long as her. I'm not about to chase if she doesn't reciprocate at least a little.

I've resisted all urges to send any further texts, and now I'm kind of just curious to see if she will ever respond and what she will say if she does. If she does ever respond, I'm not going to be upset or anything. I'll just play it by ear and keep spending time with her so long as she wants to. But if I never hear from her again, I'll take the hint and move on.

I fully get that we’ve been friends so long that maybe that’s all we’ll ever be and that's all she sees me as. And I’ve never really pursued her hard or anything like that. I didn’t do it when she visited me out of state since I didn’t want her to feel uncomfortable/trapped since she was staying with me.

I did pursue a little more this past month since she’s no longer trapped with me or anything lol. But really I only did that since she was the one who kept initiating by texting or calling me. And it was fun just hanging out with her.

I won’t chase, but to be honest I have no idea what I’ll do if she ever does reinitiate contact. If she did get back with her ex, I’m almost betting on the fact that they’re going to have another major argument eventually. Or maybe she found a new guy. But even if that’s the case, she doesn’t have the greatest track record in picking boyfriends. Most of them have been losers and criminals.

And I get it. Maybe that’s what she likes. If so, good luck to her. I’m done texting her any more until she shows interest again. Then I’ll reevaluate if she does. I don't plan to be a dick to her or anything if she does reinitiate contact, but I'll play it by ear and continue to reciprocate depending on her body language, mood, etc. I'll also try to pick up on verbal cues like if she does stuff like saying she's going to put me down as her spouse and maybe tease her back a bit if she does. Etc.

Even if things don't work out, it's honestly fun just hanging out with her. It's almost like staying in practice dating a chick or at least just hanging out with one and talking to her.

Yes, I realize I'm being overly nice to her, but keep in mind we've been friends for about 30 years. With my sobriety from hard drugs, business doing well, etc., I'm in a position to have a little fun taking her out.

For the first time in God knows how long, I feel like I'm in a good head space and can accept whatever happens. I welcome any comments even ones saying I'm messing this all up. It's very possible I am. If nothing else, I've had fun getting to know her better and spend time with her.

Slight update:

I called her four days ago, and a guy answered. He said, “hello?” I asked if she was there. She then got on the phone and it sounded like she was really sad and had been crying.

She said, “Hey, [my name.] I’m sorry. I can’t talk right now.”

I asked if she was ok.

She said, “yeah, I’m alright.”

I told her to call me when she’s feeling better, and she said ok. Then the phone hung up. I’m guessing it’s the boyfriend who hung up the phone. He didn’t talk to me other than to say hello at the beginning.

She sounded like she had been crying for a while before she talked to me. So I am guessing she is arguing with her boyfriend again. I’ll back off for now, but I’m glad I got to hear her voice. I didn’t get any hint of her being mad at me or not wanting to talk to me.

Obviously, I couldn’t get too deep into talking to her with her boyfriend there. I’ll back off and let her come to me.

I know this situation is complicated since we have been friends for so long. Although I'm not head over heels in love with her, I do think we're compatible personality-wise.

I feel like it's only a matter of time before she breaks up with this boyfriend. If she does and reaches out to me, I plan to let her know that I like her as more than friends but no hard feelings if she doesn't feel the same.

Any thoughts/advice would be appreciated.

Oops, sorry for the double topics. I'm not sure how that happened. I can't find a delete topic button. Please feel free to delete one of them.

ok i read most of it but why would u want to be with someone like this in the first place. She was getting beat up by her ex bf and she didnt leave thats toxic as hell in the first place. Shes damaged goods and doesnt know what a decent relationship is.

Women like this will bring trouble to u ur whole life. They use to toxicity and if they get into a normal relationship and since they use to toxicity and they dating someone that is normal they will go out and bring the toxicity to u. Its like an abused women they use to the abuse so when they finally date someone normal they use to the tension and that drama and since u not giving them that they will go out get drunk and cheat or something.

This woman is damaged goods for her to stay with a guy like that and have a kid with and why the hell would u want to be with someone like this. Good luck to u bro i have nothing else to add

I understand she's damaged goods. She has been in therapy, I believe. I don't know too much about that since it's none of my business.

I did sign up for a dating app just to get my mind off her, and I've chatted with a few girls. Unfortunately, most of the ones I'm interested in at all tend to live over 2 hours away. I'm not interested in long distance dating.

I will back off unless she reaches out. If she does reach out, I'll tell her that I like her more than as a friend but will understand if she doesn't feel the same.

If there's just no attraction on her part, I'll get the message and move on. If it's something she's interested in talking about/working on, I'm open to trying. I'm not going to pressure her into a relationship or anything like that and really just want to see if she wants to continue dating to slowly get to know each other more.

But I will make my intentions clear if she does contact me ever again. If she says she's not interested, I will wish her well and tell her to let me know if she ever changes her mind.

I'm in my early 40s, and it's getting harder and harder to meet women I'm interested in. I feel like all women around my age have their own issues, and I have mine too of course.

I'm a lawyer, and my practice is taking off faster than I anticipated. I will continue to focus on work. I also plan to get into working out a bit again. I've started doing pushups every day. I have a gym membership I haven't used in about a year, but I'll probably go and just walk on the treadmill and maybe lift some weights. Nothing too crazy since I feel like I'm starting from the beginning, but just doing pushups helps me get my mind off her.

If there is any interest from her, I honestly feel like she's wife material despite her past. But the question of course is whether she ever gets out of the abusive cycle with past boyfriends or if she even wants to.

Crap, I just realized a big typo in my topic title. It should be 30 years as friends to hanging out to no contact lol.

If I'm ever bored and recovering in a hospital for a few weeks, maybe I'll read this novel. Till then, nope but good luck whatever the issue is.

I would not tell her that...I think she's best as a platonic friend only....she seems to like men who rough her up a bit....

She doesn't even sound like a good friend, let alone girlfriend material. She's stringing you along as some sort of comfort blanket, and you're getting involved in her mess. It sounds like she's extremely codependent and addicted to the drama of toxic/abusive relationships. Ask yourself if that's something you really want in your life. There are worse things than being alone. Good luck to you.

^^^^^^^^^
This

it's long, wordy, and hard to follow at points but this is my conclusion; if you're going to be her friend, be her friend. know your boundaries. Friends support friends, the problem is you're mixing friendship with romance and you don't know which one you want. it's pretty obvious from what you said that she made several points of letting you know that she was interested and you did not reciprocate. you told her by your conduct you are not interested. you kept her at the friend level even though it's obvious through the reading that she was indicating she was interested in more. you made the decision whether you realize it or not. you should move on, because from her point of view you have rejected her.