Dungeons and Dragons is a social game. Despite the best efforts of a responsible DM, there will likely be times that the table talk becomes a little spicy. Flirting is part of the game and for some classes, it's a valued skill. When you meet someone away from the gaming table who shares your love of tabletop RPGs your D&D flirting skills can sometimes cross over.
These lines may be fit for a dungeon but you can try them out in the real world too. Remember to use sound judgment because in real life there are no rerolls.
10 Critical Fail
You walk into a tavern. You see a tall, dark, handsome drink of water in stunning full plate armor. Your mind races. What could you possibly say to win over this Adonis before you? You try to summon your inner bard and think of your best line. Suddenly, it hits you. You saunter over to him with all the courage in your tiny halfling and say: "Hello there, I must have failed my save against awestruck.". You wait breathlessly for the heartbeat it takes for him to react. He blushes as red as a dragon's wing. You've done it! He never saw you coming. Probably because you're 1/3 his height, but your perfect line didn't hurt.
9 Check Out The Stats On That
Talking to someone attractive can be really intimidating. The key to approaching someone is confidence. An ethereal elf at the half-orc arms dealer stands out. She is delicate, feminine and radiant. She may actually be glowing from a magical effect.
She's caught the eye of a nearby dwarf who wonders how to get her attention. Sometimes the best pickup line is simply an honest observation. He clears his throat and says: "You must have 10+ charisma". She smiles down at him and replies: "Thanks. It's my dump stat.".
8 Played Like A Fiddle
Typically, in any party, there is one character who flirts more than the others. There are several factors that make one person the flirty one at the table including player personality, character race, and even class. Anyone who's played a bard knows that flirting is part of the job description. You can't successfully fulfill the role if you don't know how to smooth talk the people around you. It's such a trope that it inspires its own pickup lines. "You must be a bard because you're plucking my heartstrings." This line is particularly effective if the recipient really is a bard. They're so used to being the ones dishing out the flirting that receiving it really turns their heads.
7 Highway Robbery
In the world of Dungeons & Dragons, even thieves deserve love. The phrase "steal your heart" may be a little creepy, but it's certainly an expression of interest. When you utter: "What's the CR to steal your heart?" there's no vaguery. You're not leaving any doubt in the air.
There's no confusion as to your intention, only your character. Typically a heart should be given freely or romantically lost. You shouldn't have to steal it. Depending on the charisma of the rogue uttering the line it could come across as either a threat or a come-on.
6 Racial Bonus
Racial bonuses are a big part of D&D. Many players choose a class and race to complement each other. "Resist charm" is pretty handy in a world where nothing is really what it seems. Not being so easy to impress is valuable in an environment where you need to be constantly on your toes. This line is perfect for any member of a race that has this useful feature: "My race is usually resistant to charms but I'll make an exception for you." It's the perfect line to let someone know just how special they are.
5 Going Berzerk
This line is a bit iffy. It would have to be delivered really well. On the one hand, it has a great reference to an iconic class. On the other hand, barbarians are more than just their rage. It's not great to start a relationship off by objectifying someone. "You must be a barbarian because you're all the rage." It has a nice light-hearted feel but it needs a high diplomacy check to land right.
4 Idioms For Days
The best pickup lines either include puns or a fresh take on a classic idiom. Every great pickup line includes an element of flattery. This smooth line combines the warmth of telling someone you find them beautiful with the fun of comparing them to a hideous monster: "I feel like a beholder, looking at you, my eyes are full of beauty."
3 Wild Night
When you hear "I hope you have some ranks in handle animal because it's about to get wild" you know you're in for something. Handle animal is meant to make it easier to train an army of spiders or negotiate an escape from wolves. The mind boggles at what it could possibly mean in this context, which may be the point.
2 Perks Of The Class
Paladins have all the fun. They frequently get to lay on hands without anyone thinking twice about it. Sure the person receiving the touch gets some perks but consent is rarely given first. "
I hope you're a paladin because I'd like you to lay on hands," flips that script. In this line, the recipient is quite literally asking for it. Nothing is sexier than consent and explicit interest.
1 On My Mind
Love often muddles the mind. It's easy for new lovers to be swept up in the excitement and get a little bit obsessed with each other. "You must be a Mindflayer because I can't get you out of my head," perfectly sums up what it's like to be newly smitten with someone. The victims of this kind of love often struggle to eat or even sleep because they are so preoccupied with the thoughts of their loved ones. Much like the long reach of a Mindflayer, love can be impossible to shake. Unfortunately, love is much harder to fight.