Reconnect with an old friend

So I have reconnected with an old friend from high school - online. We were really close, but never dated. (I liked her, was really shy - and we had a fight after a few adult beverages, and our friendship slowed to a stop). She contacted me earlier this year (she has a few times over the years, but they usually were an isolated conversation or two). This time, for whatever reason, it has stuck.

We live in different parts of the country, and she is involved with someone. We talk all the time. One thing is, even back in the day - she was always a big flirt. Today, perhaps her skills at flirting are better - but still a flirt. Many of our conversations are random - but flirting can work its way into them. We've never had "phone sex" (we talk occasionally on the phone too) or anything like that online. But ever so often she will tell me about her visits to nude beaches, things like how she just let her dog outside late at night - and she was only wearing a towel, etc. Yesterday I asked her about workout clothes - and if she felt the need to match - and she mentioned that yes, even down to the bottom level.. (Referring to her underwear). When i asked about proof - she said she is currently not wearing such an item.

We were talking about attending an event where we went to school - (neither of us live in that area anymore), and she isnt able to attend. I told her i understood - an its a far trip for a one day event - and it sounds like the event she would be going to would be more fun anyway. (The event she was going to was meeting her best friend and introducing the friend to her boyfriend for the first time. They have been dating for a few years, but he is currently living in another state). Her response to me was - yes, but you won't be there.

She tells me she is happy in her relationship with her Boyfriend, but why is she always reaching out to me? She is a major league flirt... But at the same time, many of our conversations are more normal. She confides in me about things (not about her relationship with her boyfriend, but issues with her kids, herself etc.) Conversations (mostly text) can start 6 am (for instance today) and have gone on for hours at night.

I am confused by these conversations. We have history, but at the same time - if we do actually see each other in person, it would be rare and infrequent.

Thoughts?

What history? You were close friends. You had a thing for her, but never came out with it. Sounds like you still have a thing for her and she is still in the dark about it. She is treating you like a friend and if she is a naturally flirty person, then whatever perceived flirty comments she makes are really meaningless. Frankly, she is probably fairly oblivious to the effect it has on you. On top of that, she is open with you about the fact that she is in a relationship and happy about it. I think that since you are still carrying a torch for her, you are reading way more into some pretty innocent comments than there is to read. It's only confusing because you would like more than just friendship.

To be fair, we have had plenty of conversations about why we stopped talking, and the fight that occurred. She knows about how i felt back then, and has made comments about what i should have done I am not discounting the fact that maybe i am a more reserved or conservative person - as i typically wouldn't be as open as she has been.

But we do tend to talk several times a day, (in total no less than one hour per day) - with the exceptions of every other weekend that she spends with her boyfriend who currently lives in a different state.

This is an inappropriate friendship if she is in a relationship - teasing you with stories about nude beaches, going outside in a towel - talking about her underwear -- just nope. You are being led on and possibly being groomed for someone to cheat with. if she is having long conversations with you about her life --- this could be an emotional affair. I think you need to tell yourself that she's not obtainable - she is dating someone - and you need to stop this phone friendship. Either be direct with her and say "i don't think your boyfriend would like you telling me all this, so maybe we shouldn't be talking" or indirectly by letting her messages go unanswered for a longer period of time and getting involved with other people.

To be fair, we have had plenty of conversations about why we stopped talking, and the fight that occurred. She knows about how i felt back then, and has made comments about what i should have done I am not discounting the fact that maybe i am a more reserved or conservative person - as i typically wouldn't be as open as she has been.

 

But we do tend to talk several times a day, (in total no less than one hour per day) - with the exceptions of every other weekend that she spends with her boyfriend who currently lives in a different state.

So she know you were hot for her years ago??

Back in the day, we were really close. As she described it - closer than she was with anyone she dated. Our fight occurred because i had had too much to drink, and I thought she went off with someone else. It was a misunderstanding, but at the time a lot of yelling, etc. We talked it through during our recent conversations and got past it. But, yes she is very much aware of how i felt. She has alternated in our conversations from telling me she isn't sure she saw me as just a friend vs more - to telling me i should have been more aggressive.

We've never had "phone sex" (we talk occasionally on the phone too) or anything like that online. But ever so often she will tell me about her visits to nude beaches, things like how she just let her dog outside late at night - and she was only wearing a towel, etc. Yesterday I asked her about workout clothes - and if she felt the need to match - and she mentioned that yes, even down to the bottom level.. (Referring to her underwear).

This is hillarious! She sounds interesting to say the least. What would you want to happen ? Are you going to meet or are you going to ask her to leave her boyfriend? lol x

Oh well then if she knows how you feel/felt, then this is totally inappropriate. I'd guess there is something she is not getting out of her relationship with her bf despite claiming how happy she is with him and you are pretty much becoming the other guy. It might not be physical cheating but you are flirting with this turning into emotional cheating. The time she is spending talking with you, she should actually be spending with her bf instead. Not to say that men and women can't be friends, but more that the extent of this is kind of going too far. How many guy friends do you talk with multiple times per day and discuss their underwear? It's kind of like that, the litmus test of if you wouldn't do it with your guy friends, you shouldn't be doing it with your female friends either. If you are doing it, you are probably starting to cross some lines and that makes life confusing.

If you can be just friends with her, then I suggest that you assert some boundaries. If she is looking to connect with you for more, she needs to be single first. So again, it's about you asserting healthy boundaries. You don't have to be an outspoken flirt to assert boundaries.

OK - so update. We speak most nights, but not necessarily every night. Last night - she sent me an innocent text about a conversation she had with someone. I wasn't in the mood to talk, so I ignored it. (To be fair, when i get texts, i tend to respond almost immediately to them). 2 hours later i get an emoji text from her - "Pay Attention to Me". Since i wasnt sure if anything was wrong - and at the same time, not really in the mood to speak - i sent a reply - Uh oh ... I get an emoji text back with a giggle - so i ignore. A little while later - i get a text - Ok night. I ignore.......

This morning, i get a text early this morning with - an emoji "You mad bro?" (Yes she loves bitmoji). I responded Bro? Why would i be mad? - to which she responds, Sorry - i meant to send this to her son.....

Why do i keep overthinking these things? She seemed to play off the ignore text as a joke - but im no so sure. That text does concern me a bit..... Maybe it was a coincidence the mad bro text too?

Thoughts?