I've been envious of friends who have the confidence to travel alone. I want to be that adventurous, too!
I loved being able to do whatever I wanted, eat whatever I wanted, on my own schedule. It was a special treat having no one to tell me room service is too expensive! I also loved the fact that people felt much more free to strike up a conversation with a woman out and about and dining solo.
I'm by nature a shy person, but I highly recommend even starting conversations yourself, with strangers you meet, while traveling solo. It enriches your life, and since you'll likely never see them again, there's nothing to lose! Of course, only participate in this type of activity in an open and public location.