Painful used in a sentence

Painful in a sentence as an adjective

"We wanted to make sure it was sufficiently high to be painful, but not unreasonable.

Her beautiful smile looks at me nearly every day. Some days I am glad to see that little profile picture of hers and others it is painful.

I can not believe how painful it is to develop on Microsoft tooling, and how meekly people accept it as the way it is.

The amount of privilege built into this "painful failure" is disquieting.

I'm not saying that lightly, I worked for a dozen startups, a couple of which crashed hard in the most gut wrenchingly painful way you could imagine.

While it's painful that this is happening now and not a year ago, I'm heartened that Hal is heading the internal investigation.

Previously everything was C with Libevent and it's just painful trying to get a large pool of people up to speed on using that to do their projects.

I know the HN community often stresses what a valuable learning experience this can be but there is no denying that it is a very painful affair by any measure.

I know it would be painful, and the local politics certifiably insane, but if Google wanted draw attention to the dysfunctional monopoly of the cable industry, there would be no better place to wire than Philly.

People can't predict the future, and they obviously have difficulty predicting what tools will become useful and simple, and which will become crufty tarpits of painful dependencies and incidental complexity.