Questions: Relationships

If there's someone you've been on and off with for a while (platonically) and you know they were interested in you at some level in the past... would you revisit the possibility of a romantic relationship or is it too late.

(When is it "too late"?)

Pros and cons for each:

Unhappily married pros:
1. You’re not alone
2. You have a better standard of living than you would on your own
3. She doesn’t make you happy, but she’s not a total bitch
4. She takes care of you anyway

Unhappily married cons:
1. You’re unhappy in your marriage
2. You’re taking care of your family more than yourself
3. Your achievements have to be shared with your family rather than just yourself

Happily single pros:
1. You’re happy with your life
2. You are fully independent with complete control
3. Every achievement is yours to own

Happily single cons:
1. You’re alone
2. People assume you’re unhappy because you don’t have a wife
3. Dating struggles

Pros and cons for each:

Unhappily married pros:
1. You’re not alone
2. You have a better standard of living than you would on your own finances
3. He doesn’t make you happy, but he’s not a scumbag

Unhappily married cons:
1. You’re unhappy in your marriage
2. You’re taking care of your family more than yourself
3. Your achievements have to be shared with your family rather than just yourself

Happily single pros:
1. You’re happy with your life
2. You are fully independent with complete control
3. Every achievement is yours to own

Happily single cons:
1. You’re alone
2. People assume you’re unhappy because you don’t have a man
3. Dating struggles