8 year old with seperation anxiety

My son who is almost 8 is still experiencing seperation anxiety when mainly myself want to go out.

He never has fallen asleep easily when we are out and that we have always dealt with, but lately he has been "worse". He cries in his room after we leave, doesn't eat his supper, etc. He is able to express his feelings though he doesn't know "why" he feels this way. He tells me he wants me to be home for bedtime, to say his prayers, tuck him in, etc, but he lately doesn't want to go anywhere but school without me being there too(including friends houses...he prefers friends to come over here instead).

Short of councelling, is there anything I can try first?

P.S. He is the oldest of 5 children and we don't go out often,
maybe once/month  or so. We have never been seperated unexpectedly from him, we always tell him where we are going,
when we will be home and he knows he can phone us if needed(which he has done on occasion). The babysitters are familiar to him or grandparents.

[Kevin Kennedy, Ph.D.]

It would be prudent to have him evaluated by a mental health clinician. This would clarify his cognitions and see if these contribute to his anxiety, and the consultation would also yield a management plan for you to pursue. It's best to seek professional help for such an anxiety disorder and not attempt to handle it yourself, particularly because the condition is causing him distress and is interfering with normal 8-year-old socializing.