How long should I meditate when I'm in the middle of heartbreak?

Three minutes. Seriously. Your nervous system is already overwhelmed and adding a thirty-minute sit that becomes a torture session won't help. Start with three minutes of just breathing and feeling your body. If three is too much, do two. The duration doesn't matter nearly as much as your willingness to stay with what's there. Consistency matters more than length... three minutes every day will rewire you faster than an occasional hour of spiritual escapism. Eventually your system will naturally ask for more. But that organic request is completely different from using meditation to punish yourself or prove something.

What if I start crying every time I try to meditate?

Then you're doing it exactly right. Those tears need to move. They've been dammed up behind your professionalism and your social media presence and your insistence that you're fine. Let them come. Cry through the whole sit. That's not a failed meditation... that's a successful release. The only thing I'd add is to pay attention to the tears somatically. Where do you feel them before they fall? Is there a trembling in your chin or a thickening in your throat? Stay with the physical sensations even as the tears flow. This keeps you from drowning in story and anchors you in the body's wisdom.

How do I know the difference between staying present and wallowing?

Wallowing has a quality of drowning. You lose the witness. You become the story entirely with no part of consciousness observing it. Staying present means there's still a you that's aware of the pain happening. Wallowing loops without resolution. Presence allows the energy to move and shift. Also check your intention. Are you replaying the narrative to punish yourself or to really feel what needs to be felt? The body doesn't lie. Wallowing usually involves tension and constriction. True presence has a quality of softening and expansion even through the grief. If you're tightening up, pull back. If you're breathing and letting waves move through, you're on the right track.

Can meditation really help me stop obsessing over them?

Not by stopping the thoughts. That's the trap. Meditation won't magically delete them from your consciousness. What it does is change your relationship to the obsession. Instead of being hijacked by the thought every time it appears, you start to see it coming. You recognize the trigger. You feel the compulsion to check your phone or stalk their Instagram and you breathe through that impulse instead of acting on it. The thought still visits but it stops being the landlord. It becomes a tenant... sometimes a noisy one... but a tenant that doesn't control the house. Letting go of attachment happens through presence, not willpower. The less you feed the loop with action, the weaker it becomes.

What if I can't forgive myself for what I did?

Then don't try to forgive yourself yet. The pressure to forgive before you're ready is just another form of violence. Start with something smaller. Start by just acknowledging that whatever you did came from a part of you that was in survival mode. Not to excuse it... but to understand it. The part of you that sent those desperate texts wasn't your wise self. It was a terrified inner child who believed without this person they would die. That part doesn't need forgiveness yet. It needs to be seen. It needs you to stay present with it. Go back and read the section on forgiving survival mode behavior. Forgiveness is not the first step. It's the fruit of a long process of presence. Let the process take its time.

The Radical Act of Staying: How Meditation Heals Heartbreak by Teaching You to Be Present With Pain