You have gone to great lengths for love, whether you were successful in your endeavors or not. You may have a spouse you would give the world to, be willing to go on entire journeys to earn your beloved's hand, or even attempt to break the laws of nature to revive your lover from the dead. Perhaps your feelings are one-sided, and you are seeking to prove your worth to someone, or you want to become famous to have a shot with a parasocial paramour. Hell, maybe your devotion isn't even single-minded (or single-targeted)and you go head over heels for most any potential sweetheart you happen upon!

Skill Proficiencies: Performance and either Perception or Investigation

Tool Proficiencies: Pick 2 from one set of artisan’s tools, a musical instrument, or a language of your choice

Languages: None

Equipment: A token of your beloved, a notebook and writing utensil, artisan’s tools or a musical instrument, a set of common clothes, and a pouch containing 10 gp

Being a hopeless romantic is almost always, well, romantic, and oftentimes necessitates a significant NPC. Talk to your DM about what kind of parasocial options may be included in their campaign, and about exactly how far your character will go for their sweetheart. If you would prefer your character not to hold romantic feelings, the options on this table can be interpreted platonically!

Personality Traits (d8)

1	I don’t much care for conversation with anyone but my beau.
2	I have trouble keeping money in my pockets instead of spending it on gifts.
3	I adore physical touch, and love sharing it with others without thinking whether it's welcome first.
4	I like to give my full attention to whatever I’m doing, and think that dedicating time to something is the best way to see results.
5	I can find something to compliment about most anyone I come across.
6	If there is a task that needs doing, I would rather do it myself than leave it unresolved, even if it isn’t my responsibility.
7	I tend to let my mind wander more often than not, and often have my head in the clouds.
8	The only thing I love as much as my beau is drama. Whether I cause it or not, witnessing it is always a pleasure.

Ideals (d6)

1	Communication. Open and frank discussion is the most effective way to talk to people. (Neutral)
2	Respect. Boundaries are the cornerstone of civilized interaction. Crossing them is unthinkable. (Lawful)
3	Consideration. Thinking of others as often as I think of myself makes everybody happier. If everybody was more considerate, the world would be a better place. (Good)
4	Passion. Something filling me with emotion is good enough cause for me to pursue it, no matter what it is. (Chaotic)
5	Possession. The end goal of a relationship is to exert power over another person. (Evil)
6	Happiness. Everybody is just trying to find a source of joy, including me. (Any)

Bonds (d6)

1	My beau left me for another person. I don’t know what I'd do if I ever saw either of them again.
2	The place I first met my sweetheart is as precious to me as my home.
3	I have a child, but with someone other than my current beloved.
4	My beloved is deathly ill. I only have so much time to find something to help them.
5	My beau’s parents have been there for me more than my own ever were.
6	My older sibling taught me everything I know in the art of courtship.

Flaws (d6)

1	I believe my lover can do no wrong and trust everyone that claims any relation to them at all.
2	I often lie to those I care about for the sake of getting their admiration and praise.
3	I am obsessed with physical appearance, both in others and myself.
4	Beau or no, I can’t help flirting with anyone who catches my eye.
5	Oftentimes I'll choose whatever option I find the most fetching or romantic, regardless of whether it's a practical decision in the slightest.
6	I would abandon everyone and everything else in a heartbeat if I thought it would please my beloved.