Some say love is blind and ageless, but a sustainable relationship is built on a lot more than just love alone. Just think about having children in your thirties, and chasing around toddlers with a man in his late forties.

It takes a certain amount of compatibility to carry you through the decades ahead. I hear that you are an old soul, but that doesn't necessarily mean you have to date someone significantly older to meet your "soul-match." I say go for a five to seven year age difference.

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You are creating your life while he is already in the prime of his.

If you were 40 and he was 55, I would not be as concerned about the age difference as both of you would have had ample time to experience life and mold your identity.

It's really a case of two kindred spirits being separated by a lot of numerical years. - Old Soul, 27 Just the fact that you are presenting this question makes me wonder if you already know the answer.

If I follow what feels right, am I setting myself up for future failure? Usually, we don't question the things we know in our gut to in our best interests.

If Mary Kate or Ashley was approachable and not icy fashion prodigies, I would love to ask how they make it work. After it ended, he talked to a lot of people about our relationship -- and what happened through the grapevine was unexpected. Women judged me as having an ulterior, economic motive: “She just dated him for his money,” or “She thought she could get ahead.” In our society people are so quick to judge a young, naïve woman -- never the older man who perhaps should’ve known better too. I have a friend who’s been married to someone for more than a decade who is 20 years older than her.

In my case, the age gap was actually a cavernous black hole defying space and time. Another lesson in dating: a fling with someone in your professional/personal circle is more often than not bad news. He’s old and sick now, and she takes care of him (even financially), but she’s still partying and sleeping around. I sometimes imagine what would have happened if I had stayed with my older man.

He's had a heck of a lot more life experience than you have.

You are in your late twenties, a time in life when you are just beginning to become sure of who you are and what you want.

A word of caution though, if you think and anticipate failure, you will surely achieve it!

" I echo her word of caution and circle back to the simple truth that you are having doubts.

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.