Being less pessimistic about dating requires that you avoid judging new dating prospects based on negative experiences that you have had in dating in the past.
It can be difficult to do this because as human beings, we tend to use our past experiences to prejudge people.
If you aren’t a workaholic yourself, you may find it difficult to sustain this kind of relationship.
If you have a good amount of free time on your hands outside of work, you could become very dissatisfied with the fact that the person that you are dating is at work and not hanging out with you.