What kind of meditation do you do? Do you do metta? If so, maybe just smile, relax, visualize your spiritual friend, and wish them well. Feel the wish that they be well. This is what I do on my daily walks. If you know you're feeling the wish, that's fine. If the feeling fades, you might subvocalize again to make another wish for their well being to help bring the feeling back up.

It sounds like "The Inner Art of Meditation" by Jack Kornfield is someting like what you are looking for.

But that is not what I do. My suggestion is to breathe in a relaxing way, relax as you exhale, relax as you inhale, notice the pleasant feeling of relaxation as you inhale and exhale. If you feel tense, try to relax the tension. Notice what makes you tense and what helps you to relax. You can do this sitting, walking, washing the dishes etc. In addition to meditation, explore different types of relaxation exercises.

My view is that dukka = stress. Understanding the origination and cessation of dukkah/stress (the 2nd & 3rd noble truths) is what leads to reduced suffering.

"If you could be relaxed in every situation, what would that be like?" You could take this as a koan, it might be helpful.