
Dear Sugar,
When I broke up with my boyfriend, I was devastated. We were head over heels for each other but things just weren't working out so we ended it. At one point when I was trying to get over him, I threw away all the pictures I had of him and us, all the CDs he made me, and anything that reminded me of him.

As far as sharing
relationship histories with each other, I tend to believe that some things are better left unsaid. But just because you're not saying it, doesn't mean you're not thinking it. Considering your past relationships in contrast to your current situation can actually help to illuminate the good things you have now or the ways you've changed.

When we're young, most of us know very little about ourselves, let alone what we want out of our relationships and from our sexuality. So in our earliest relationships, it make sense that we're still in the process of discovering who we are, which is why I don't find it at all shocking when people mention that one of their exes later came out. Has this ever happened to you?

Sex can be a very impulsive act — I mean, that’s where some of the fun comes from — but that kind of passionate spontaneity can also lead to second-guessing later on. I’m a person who likes to believe that everything happens for a reason, and any mistake is just another lesson learned, but there are still things I regret. We can't take things back, but wouldn't it be nice if we could have a few "do-overs"?

You’ve met the guy of your dreams. He’s funny, smart, kind, and totally into you. After meeting through a mutual friend, you enjoy the most romantic date ever the very next night.

Dear Sugar,
I dated someone for almost three years until he started to feel less for me. We thought we solved it, but a week later we broke up. We continued to hook up afterwards, but it didn't take long for him to date someone else.

While I definitely have a penchant for curiosity, I also know when to draw the line. And when it comes to a budding relationship, many things are best left in the past. It’s true that meeting a new love's ex love may satisfy my prying mind, but in the end it only leaves me wanting more or feeling inadequate.

While the majority of you may be skilled at keeping history
right where it belongs, there are certainly some things from the
past that once known, require a lingering thought or two, like children from a previous relationship, a traumatic incident in childhood, or cheating.
Though I don’t think the familiar catch phrase
“once a cheater always a cheater” is necessarily true, if I found out that a significant other had cheated in a previous relationship then I would be concerned. But perhaps I’m just paranoid, so what do you think?

Though it's nice to believe that when you meet someone new you’re each starting with a clean slate, the truth of the matter is, you’re both bringing your own mix of good and bad past encounters to the table. When it comes to love, a person can't help but approach things with her own experiences in mind.
Then again, if you find yourself falling for someone, it’s only natural to give him the benefit of the doubt even if his history might tell you to run for the hills.

I have been in my current relationship for about a year, but I have known my boyfriend for four years. We were friends before getting together, and I actually knew him throughout my last relationship. During the time before we were together and after my last relationship, I jokingly, and perhaps teasingly, made references to the sex life with my ex, who was always convincing me to try something new.