Regularity and Weight Loss

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Okay, so I am not a very regular person. I tend to go DAYS at a time without a bowel movement. Even regular consumption of fiber pills and probiotics does not help very well. I'm assuming it's a bad mix of my medicines (Synthroid and Metformin) along with my less than ideal diet at this point on my journey. The last time I was consistently regular was a few months ago when I was visiting a chiropractor a few times a week for readjustment of my neck (my neck is curving the wrong way).

First, I'm just genuinely curious how much being regular plays a part in weight loss - whether it be on the scale or in measurements. I'm assuming it's pretty important, but I don't necessarily want to buy into a myth or anything either.

Second, do you have any tips on how I can get my bowel moving in the right direction (pun definitely intended)? What would you say are the best foods to incorporate into my daily diet? My mom tells me cherries, but I haven't had much luck with them either.

Any help in this, somewhat embarrassing, matter is much appreciated!

Oh and one other bit of information, sometimes my lack of regularity leads to about 8 hours of IBS-like symptoms. I'll start constipated and then have diarrhea and cramps and it sometimes it is so bad that it quite literally feels like death :embarassed: So, yeah, I'm pretty ready to get rid of this problem. Do you think I should be concerned enough to see my doctor about this? (Although I've told him before and he acted like it was normal.)