What is the best way to deal with an insecure boyfriend with trust issues?

From my experience I tried to be extra loving and reassuring, but that still didn't work so eventually he drove me crazy by putting himself down and accusing me of looking at other people and not trusting me in general.

If you have the love and the tolerance then just reassure him that he can trust you and be a trusting girlfriend and love him and if you have it in you try to compliment him or do something sweet for him now and then.

If that isn't working for you then talk to him about it.

If that doesn't work then you may be out of options.

I'm sure you already know the answer, you just need to think carefully about your relationship and you will find the solution.