Okay, so thanks to your pre-posting questionnaire, I can tell that you’re 44 and he’s 59 and you’re two men who are divorced, both with adult children from prior relationships. So, here’s the thing — the age gap isn’t that big a deal. I don’t think this is a “daddy issue”. You’re both divorced with kids — that levels the playing field and can shorten the gap between your ages. Plus, you work at the same place, so that’s another thing you have in common! That said…. you work at the same place — and there are implications if things don’t work out between you. You’ll have to see each other and focus on work when having an ex in the office can be a distraction. However, most people spend a lot of time at work, so it’s normal to meet dates there. If you can handle the work romance dynamic, then I think you should ask him out on a date, and break the pattern of flirting without commitment. Think about the worst case — it’s really not so bad, is it? 🙂
