I (46F) dated this guy “D” (42M) really briefly when I was 24 and he was 20. I was actually his first. Not long after, he joined the military and got deployed overseas. We wrote letters back and forth for a while, and recently he told me he’s kept all of them — even 20+ years later.
In 2008, when he got out, he looked me up again hoping to start something up. The timing sucked because I was moving out of state in a few weeks, so nothing really happened.
Fast forward to this summer (June 2025), he reached out again. Now we live about 1,200 miles apart in different states, but since then we’ve been texting literally every day and having weekly phone/video calls that last like 2 hours. It feels really warm and flirty and honestly relationship-ish.
The confusing part is:
He got out of a 10-year relationship about a year ago.
Early on he told me he’s in therapy and “not ready for a relationship.”
But the way we talk and the consistency of it feels like it’s more than just friendship.
He also has two young sons. I’m single with no kids.
The thing is, I can feel myself really falling for him, and I don’t want to get too deep in without knowing where he stands.
So now I’m wondering… should I ask him directly how he feels about me/what this is? Or should I just let it keep unfolding naturally? If I do bring it up, how do I say it without it coming across as an ultimatum or scaring him off?
TL;DR: Reconnected with an old flame ([46F] & [42M]) after 20+ years. We text daily and have weekly video calls that feel relationship-level, but he said he’s not ready for a relationship. I’m falling for him and don’t know if I should ask where we stand or wait.