Question for women I've got to start at the beginning. My ex (first love, lost virginity to) cheated on me with multiple people. Naturally I left her but took a pretty big hit emotionally. Less than a month later, my mother passed away. I've moved back home to care for my sick father, and subsequently lost my job driving tractor trailers over the road. It's been 5 years and I've fought depression between those things and just didn't think of myself as being "date-able" without having a job. Now, my father is well enough that I can resume working elsewhere. Here's the question; would a woman find my gap in relationships acceptable? I haven't had steady employment, I know that doesn't look good for a potential partner, but maybe the reason I have missed work makes it somewhat better? On top of all that, I don't know how to date. I was with the same person from 8th grade until I was 24 years old, I don't know what to do. Talking to a woman is hard, asking them on a date would make me faint! Thanks for reading if you've made it this far. Criticism is acceptable but please don't be rude.