In case you missed it: Yesterday's letter writer added an update in the comments section at 3:41 pm (I posted her comment).
I have a group of friends that does everything together. Over the past six months, though, I've become much closer to one of my best guy friends from that group. We started hanging out alone, he would always call me to do something or just chat, and we would text all day, from the moment we woke up until we fell asleep at night. He always sits next to me — he makes up an excuse, shifts seats, or switches with other people just to be closer to me. I don't always respond nicely to that; I act like it's unnecessary. I don't know why. He takes candid pics of me, and I've randomly caught him staring at me. He teases me all the time. More recently, he started "joking" (I'm not sure if it's joking or hinting) about adapting our personalities to match better so that our relationship can work out.
I've been traveling this summer to visit family and he's spending his summer at the beach with our group of friends. The problem is that I think he's back with his ex whom he never loved. He used to date this woman because he thought she was "convenient." He broke up with her because she was very clingy, and that's when we became really close and the flirtation increased. If she called when I was around, he would ignore it and say it didn't matter.
Now that I am away, we've started talking less than before each day, but we've still made sure to update each other and talk daily. When we didn't talk for a couple of days, he called me internationally and gave me a lecture about reaching out, saying we're not just friends like we everyone else. Two days later, I find out that his ex started hanging out with the group again. That's when we suddenly stopped talking. Then he texted me that "we need to talk," but we never did. I don't know if they're back together or if he's just having a summer fling. It's all so confusing to me. Does he like me but he's confused? Or could it be that I'm just a really close best friend? What's really going on?
It sounds like he has feelings for you but that he hasn't known what to do about them. It also sounds like he is still attracted to his ex, and that he was happy to have some companionship while you were away for the summer.
That's just a guess, though. Only one person knows what's going on in his brain.
My advice: When you get back from your trip, tell him that you need to have an honest conversation about your friendship. Ask him whether he has a girlfriend and how he feels about you. Give him some honesty in return. Tell him that if he's single, you'd like to give this romantic relationship a try. If he's not single, explain that you need to set some boundaries so you don't get confused. You shouldn't have to spend any more time wondering where you stand.
Readers? What happened this summer? Should she want to be with someone who got back with a "convenient" ex?