However, maybe you've met a woman you really vibe with, and she's younger but not too young, and you've talked about everything — your expectations, where you are in life, your goals for the next few years, etc — and you're aligned. If I follow what feels right, am I setting myself up for future failure? Again, though, these are not hard and fast lines or rules, and you need to draw your own moral lines. By dating someone so much older, you are missing out on being with someone who is in the same phase of life that you are; someone with whom you can share the joys and pitfalls of discovery. I forwarded your question to Dr. Which is all well and good, except if you're as directionless and financially insecure as the men she's trying to avoid.