My girlfriend and I broke up. At first, it’d seemed like nothing could go wrong. Her whole family, and friends accepted me.

Her friends said she was starting to fall for me. But then I felt she was hiding stuff from me. She said she wasn't.
A week later she gave me a day-long test, because her friend thought I was hot. So she distanced herself from me to see if I'd flirt with her friend. I passed the test.

The next day, she was again distancing herself, so I gave her space and came back finding her alone with this dude.
When we eventually started to talk, she doubted us as a couple, saying that she pictures me with her friend.

I later learned she still had feelings for that boy she’d been with. I blew it out of proportion.

She said I should’ve trusted her that nothing would happen between them. We both cried. She felt we rushed all this, and it’s too stressful for both of us.

Finally she said she doesn't want to break up, we just got to get to know each other.

I kept pushing to make things work and I believe I drove her away… asking do you really want to work things out, and if she still liked me?

She said she still had feelings, but a lot’s going on and I’m going through a lot. I finally pushed for a definite answer.

She said she thinks all we could be is friends, maybe, as she’d started talking to the other guy.

The next day I messaged her that I want to be more, and apologized for questioning us and not trusting her.

I said I'd love a second chance someday, a fresh start.

I’ve had no reply and fear I've lost her forever, and I’m in love with her and would do anything to get her back.

Desperate

The daily doubts, tests, distancing, and discussions add up to a relationship that never got off the ground. Neither of you felt secure… it was too fast, too intense, with too much analysis, and then backtracking.

You both need a break from the pressure of trying to know if you have something worth trying again, or not.

You both seem young and inexperienced in relationships beyond early dating. That’s normal; so don’t push it to places you don’t know yet how to handle. Nothing, including the breakup, is forever at this point.

If you contact her, do so without pressure or questioning her about the future, just occasionally checking in as a caring friend.

Let time help you both get more confidence about yourselves, and handling relationships, before you talk about trying again.

My close friend hung up on me one day without saying why she suddenly got angry. I called, texted, tried to apologize for any offense, but got no reply. Several months later, she called and acted as though nothing happened.

I’ve wanted to know what happened, but when we talked again, she said her parents were divorcing. The conversation was all about her hurt, and sadness, so I didn’t ask if it was related to her hanging up that day.

Is it wrong for me to pursue this now?

Still Wondering

Drop it. She shared a personal and emotional family crisis with you, and that shows her trust and feeling of friendship.

The hang-up could’ve been for many reasons, related to her dealing with her parents’ story.

My female friend of several years, 29, used to be close but due to distance and life events, we’ve become occasional text and Skype acquaintances.

Her relationship (one year) was troubled; she’d only contact me about her problems. She’d rarely ask about my life. He broke up with her in April.

She still keeps asking, Why he did this, how could he have another girlfriend, etc.

She’s miserable because she can’t get a job, or find another boyfriend.

I’ve tried to be supportive, but I’m over rehashing these issues.

How can I put an end to her analyzing this situation, without evoking her mean side (she can be spiteful and we know the same people)?

End Contact? 

Delay contact. Say you’re busy, will respond in a few days. Then do, with fulsome chatter about your own life. When she raises the old questions, say “I don’t know,” and keep talking about you.

She’s too self-interested to stay connected.