The expected value of not asking someone out is zero.

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The expected value of asking someone depends on a few things

1. your pre-nup policy
2. the other person's wealth

The outcomes are:

1. you get married and never divorce, adding that person's wealth to your own
2. you get married and divorce, and you have to give the other person half
3. you get married and get a divorce but don't have to give up anything cause pre-nup
4. you don't get married

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50% of marriages in the US end in divorce or seperation.

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The expected value if you don't sign a prenup is ((your wealth their wealth) (-your wealth/2)) / 2

The expected value if you do sign a prenup is ((your wealth their wealth) 0) / 2

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So if your pre-nup policy is that you will definitely make them sign a prenup, the expected value of your marriage is always positive as long as you have positive wealth.

Otherwise, the expected value could be negative :(