If I am hypoglycemic am I at high risk for diabetes?

Reactive hypo, yes. Many patients with reactive hypoglycemia (happens after meals), especially younger women, have underlying Insulin resistance. They experience hypoglycemia due to excessive pancreatic release of Insulin after ingestion of high-carbs or fast-acting carbs. Excessive Insulin release causes hypoglycemia ~1-2 hours after meals. Ultimately, the pancreas wears out, and these patients get diabetes.
Perhaps. There are different forms of hypoglycemia. The most common is called reactive hypoglycemia in which the sugar rises high and then dips low a few hours later. My personal view is that this is an early stage in the development of diabetes. If you go the exercise and diet route this is not a high risk, however.