So long story short, about four years ago I met this girl in her late 20's, a single mom to a baby, and they lived a few hours away from me… the father of the baby walked out on them about six months earlier… we met online and began chatting, and then we had a phone call and got along well.
Over the next few months we hung out multiple times, she was going through a deeply difficult time and i helped her with groceries, bought her and the baby gifts, we all even went on a trip to my parents winter home in a very beautiful tropical climate, and she had an incredible time… she never really traveled, so this trip meant the world to her.
In her words, she never met someone who was so kind and selfless, supportive like i am. She really valued me as a person, we had some wonderful, deep and personal conversations.
A few weeks after the trip, the father of her child walks back into her life after one year of absence… over the next three years, he cheated on her multiple times, a very back and forth rocky relationship they had… she continues to take him back…
As soon as he walked back into her life, time hanging out with me was put on hold because he was jealous of me, and she hated to do this, but our plans to hang out were put on hold for a time… we met up once a couple month later, all three of us and we all got along well… but after that, jealousy again took over and he didn't like her hanging out with me…
And then when he cheated soon after all this, the boundaries of hanging out with someone of the opposite sex became even more strict, so we have only kept in touch through messaging for the past three years.
I have remained supportive and kind, pouring into her for those first three years… even sending her care packages at times, which she deeply appreciated… she still feels the same way about me and values me a ton, but the dynamic with the father of her child/her boyfriend complicated things.
early last year, she reached out and was really interested in talking to me, it was like the days before her baby daddy walked back into her life, we were talking so normally throughout the day and it was so refreshing…
a few days of that, i got excited and missed her, and asked to hang out with her… and she obviously couldn't due to the nature of the boundaries she has with hanging out with guys now that she's working on her relationship with her baby daddy… this hurt me a lot, and i expressed to her the emotional toll that took on me… it seems her and i can't really talk much without me getting hurt… she wants to hang out, but she has to respect her relationship with her baby daddy.
After that, I backed away and a few months later, late last year, she reached out to make a serious effort to talk personally with me, and rebuild our friendship even if it's just through messaging…
So we did that for a few months and it went well… only for her to not be able to keep communication up on her end… she was afraid to talk to personally with me, solely because she doesn't want to hurt me… she was very cautious not to hurt me again, and her life is incredibly chaotic, so i just backed away like nine months ago, the longest we've gone without talking.
A couple weeks later after i backed away, she posted a picture of her wearing some clothes and gifts that i bought her on the trip we took, which she rarely does… so that was a positive thing to see.
I know she values me and enjoys talking to me, but she also feels like a burden to me due to not being able to hang out these past few years… and that's likely why she also hasn't reached out these past nine months; feeling like a burden and cautious to not hurt me.
for the first time in nine months, i contacted her… the other day i sent her a photo of me on a recent trip i took, and then i send her a brief msg casually saying something like:
"hey just wanted check in, there's me in florida over the summer… all is well, i moved a couple months ago… been a great year for growth… i'm going to continue to remain at a distance like i have since december… hope you're doing well"
i know her life is incredibly chaotic, and this feels like a safe email to send… did i send a good 'reconnecting" type of msg? what do you think?
tl;dr reconnecting with old friend