My now-husband and I have been together since we were 16, so the beginning of our dating life was a little unorthodox. Remember, when you're 16, "dating" doesn't always mean "going out on dates together." So we technically "dated" for a while (i.e., hung out at each other's houses, made our coupledom known around campus) before we actually had our first night out together as a twosome. Finally, on our first Valentine's Day together, we headed out to a local Mexican restaurant. I was nervous, it was fun, and we felt very adult and romantic. Until the time came to pay the bill, and we both stared at each other in a panic — neither of us had thought to actually bring our wallets.
We called my dad, he arrived with cash in hand and saved the day, and our date was semi-salvaged, although we were both humiliated. First date: somewhat disastrous. The 15 years since then: pretty damn good.