That’s the type of question that really depends on the person, the situation, and the Rav you are asking. Personally, I am very honest and I try to stay far away from dishonesty (emphasis on the word “try” – it’s not as easy as it sounds).
I have a friend who was an older single girl. People kept pressuring her to lie about her age for shidduchim, telling her that it is permissible for the sake of shidduchim. Finally, she asked Rav Sheinberg, zatsal, (he was her Rav) what she should do. He said to her pointblank, “It’s assur to lie.” I think he said it in a tone of voice as though it’s a clear-cut thing, and why was she even thinking of asking.
She was mortified. She hadn’t really wanted to lie in the first place – she only asked because everyone was pressuring her so much.
Rav Sheinberg, zatsal, was known for his honesty. I had my own story with him. Maybe I’ll write about it, but this post is long enough.