Going Away and Leaving a Timid Cat alone

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I have been going to see my boyfriend on weekends for several months now with our long distance. I never planned on having to do this so much when I got my kitty. I will spend almost two full weeks every day and almost every moment with him and then I will leave for 3-4 days. Sometimes when I visit my parents I even bring him too but it's hard on him. He hates it when I am packing, he knows, and then he hides. Well I plan on going away for a few more days again. Even if I have my mom take care of him, he gets no attention. Now my cat when I am home will sit on the couch right next to me... when I'm in bed he's right next to me by the pillow and even when i'm in the shower he sits on the bathroom rug. I know how attached he is and so when i leave for 3 days... and on a rare occasion 5 days, even if he has someone to come in and say "hi!" and feed him and water him... I feel bad. In 3 weeks the travels I have been dealing with will come to an end. I have only had to be doing this for a few months but I feel terrible for them. He's a good cat, he doesn't destroy my place when I'm gone. The times my mom watches him she says he just sleeps in the closet whenever she comes in to say hi and she can hear him playing with his toy at night. I guess my main question is... When looking up information about how to deal with spending time away from your pet people suggest to have a friend or family member come and check on him to make sure he's okay and feed him. People say this is not only important to feed him, ect... but also so that he doesn't feel completely alone. But, what do you do if your pet is so timid from strangers he won't interact with anybody so he just ends up being utterly lonely for 3 days. I can't wait til I move towns... I feel so guilty for being away from my cat for even a Thursday late evening til Sunday morning. I guess since in a couple more weeks I will no longer have this issue it may not matter so much now. I thought about getting him a playmate once. He likes my boyfriend but his apt doesn't allow pets... so there is hope for him to like other ppl I guess. I sometimes leave music on for him and i leave some clothes of mine on the floor so my scent is still there, I heard that helps.