I dated a girl a couple of years ago and thought that she was “the one.” She was always kind of reluctant to be serious.

We broke up five times over the year or so that we dated.

She ended it right before I started law school in 2013, but got back with me right before it started.

This was the first time we'd be in different cities and it quickly fizzled out for good.

Our final break-up hit me hard, and it took me at least another year to somewhat get over her.

That following year, I attempted to reconnect on Facebook before she began law school in a different state, but she was somewhat cold (understandably).

I tried to show her that I’d changed a lot and wasn't the guy I used to be.

She essentially said that she didn't have time for me, given that school was starting.

I gave her my number and said to contact me if she needed help with school (hoping she'd just want to talk).

A month later, she texted me asking for help with an assignment.

I gave her some cursory advice and asked her if she'd like to talk on the phone some time soon. She never responded.

After three weeks of my waiting for a response, I blocked her from my Facebook. Eight months later I unblocked her, and randomly, she added me.

This was just days ago. She’d liked a few of my older posts but hasn't reached out for a conversation with me.   What should I do?

Friends are saying I should just ignore her, but there hasn't been a day since we split that I haven't thought about her (though I've been in other relationships since then).

So many things are triggers that make me think of her.

She goes to school in Oklahoma and I go to school in Texas so the distance between us would be greater than ever before.

Should I attempt to reach out to her?

Always On My Mind

You’re still emotional about this woman, so it depends on why, and on what you can handle.

Reaching out is fine, so long as this isn’t all about feeling rejected in the past and trying to make it right by getting her back.

She didn’t reject you. She wasn’t ready for the depth of relationship you wanted then. Both of you had serious education goals ahead, with years of study.

And the long-distance situation would’ve made a committed relationship even more difficult.

That was then. Now, “reaching out” has to be slow, casual, and friendly - not a bid for getting back together soon.

If you can manage to be easy-going about how quickly she responds, whether she’s available for talks, etc., you may re-build a connection.

That’s all you should be trying for, at this point.

Don’t suggest visits and anything more involved unless, and until, you have a real sense of her being interested in more than friendship.

Your friends are wrong. You’re the one with feelings. Just don’t build imagined expectations.

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Last month, my best friend and I ate at a restaurant where the owner flirted with me, which I enjoyed.

He provided his phone number, and then connected with me on social media. My friend and I were giddy about what this connection could lead to, believing that he was interested in me.

He and I live in different cities. We’re not in a relationship, but we're in contact.

Recently, my friend said she's going to connect with him. When he accepted her social media request she said she should go back to the restaurant, i.e. without me. I'm quite annoyed.

Do I say something or let it go?

Un-Friendly Move

First, make sure your assumption’s correct that she’d go alone. If so, express surprise since you both discussed your having a potential relationship with him.

Unless he told her that wasn’t happening (and she should’ve told you), she’s crossing the friendship line.