Is it crazy to never take a single holiday in your working life, retire at 65 and then travel all the time?

Can someone truly love you and still choose to leave? Or does leaving mean their feelings were never strong enough? What do you think?
What if I went on a date while my boyfriend and I were on break? He hurt me so bad that time. I thought we were over. Should I tell him if we gonna get back together or not? He might be real upset about this.