(Note: the situation described below, would have been typical for the High and Late Medieval period)

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There’s a really cute guy I’ve seen at Sunday mass that has caught my attention, and I think I’ve caught his.

First off, it´s highly unlikely you are only just noticing this particular guy. Medieval villages tended to be small affairs, typically they rarely exceeded more than a 100 inhabitants and many were related to one another to various degrees. Most typically, you would have known him for quite some time already. In fact, in addition to him, you would have been quite familiar with his relatives as well and it's not unlikely you yourself would be related to him.

To be fair, unlike contemporary villages, most medieval villages tended to be clustered more closely together so you would have definitely known many more people than those living in your particular village and though it would be possible to meet a complete unknown (perhaps someone moving in or passing through from one of the more distant neighboring villages with which you are not that familiar) but would have been, again, unlikely.

What would a (first) date(s) look like? Would I have to be accompanied by a trusted female friend/family member?

Courtship (calling it 'dating' would be anachronistic) between peasants was a relatively simple affair, especially if the people involved were not particularly affluent or free peasants. The man would present the girl with simple gifts, for example food or clothes, to make his intentions clear. A typical food gift would have involved fruits or a maybe a festive gingerbread-like biscuit. The gift-giving was more of a traditional aspect though, as the woman involved would have been well aware of the mans intentions prior to this due to earlier flirtatious behavior. Both could initiate flirting (a peasant woman would not be considered a harlot for such behavior) though it was more expected of the man.

There was little secrecy and the flirting and gift-giving would typically happen in public, for example while working the fields together, while walking in to each other in the village square, during a feast (for example the kermesse) or at the wedding of a friend or relative.

As a general rule, as social status increased, so did interference with marriage. So if the social status of the man was higher than yours, for example with yours being that of a peasant and him being (the son of) a free tenant, then this would have complicated the matter. If he was the first born son of a ´regular´ peasant, then this too could have complicated the situation, though to a lesser degree.

For how long would we date? Is a breakup an option?

The courtship period could be fairly long depending on the age of the people involved. 'Breaking up' was a possibility, even if there had been sexual intercourse, which was of a far lesser significance among the lower classes than it was among the nobility. The main 'deal-breaker' however (in regard to both the length of the courtship period as to sexual intercourse prior to marriage) was pregnancy, after the onset of which the two parties were generally wed as soon as possible.

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What would my wedding look like?

Medieval peasant weddings were unlike modern Western marriages, in which the focus is clearly on the couple getting married. In contrast, medieval weddings were mostly communal affairs. There would be a small ceremony in the local church (occasionally as a part of a larger Sunday mass) followed by a feast, generally paid for by both families. The Peasant Wedding by Pieter Bruegel the Elder, gives a nice impression of such a feast.

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Further reading:

• Law, Sex, and Christian Society in Medieval Europe, by James Brundage
• The Ties that Bound: Peasant Families in Medieval England , by Barbara Hanawalt
• Medieval Households, by David Herlihy

Thank you to the two posters who answered my question with so much detail, it is much appreciated!