What song would you play for a woman you were trying to romance? Would you sing too or would you just play the guitar?
I wouldn’t do anything like this personally, but a good suggestion that fits the bill would be ‘To Make You Feel My Love’. Pretty easy chords to play, pretty easy to sing, and a really smart, beautiful and romantic song.
To make a long story short, once upon a time I did this; I wrote a song, drove down to Boston where the said object of my affections lived, contrived to meet her on Boston Common without her knowing I would be there, and played this song for her.
It didn’t work.
But don’t let that stop you! 
ianzin has a great suggestion, that’s a really nice tune.
How much time are you talking? A song that women seem to go crazy for (and it is a beautiful song) is Dire Straits’ Romeo and Juliet, though it might not be exactly appropriate.
It all depends, of course, on the woman. If you’re interested in her, you should have at least a vague idea what sort of music she would like. A goth lady doesn’t want something sappy. A soccer mom (probably) doesn’t want metal.
Sing as well as play, if you’re up to it. Most people are more taken with singing than just instrumental music.
VeryCoolSpouse is darned near tone deaf, but always appreciates it when I learn a special song that she likes. Billy Joel’s “And So It Goes” has been a big favorite lately. You (almost) can’t go wrong with Billy. That one is not for the beginner, however.
Well, I know this is probably not at all what you’re looking for, but the first song my man played (and sang) for me was Weird Al’s “Yoda”.
It worked, but I’m just nerdy like that.
I’m a nice guy, but
I don’t
Love you
I just wanna sleep with you
–Wall of Voodoo, Can’t Make Love
Sorry. First thing that came to mind.
If you have the voice to pull it out I’d play (in theory, I have no talent in real life) “Sleeping to Dream” by Jason Mraz.
“More than Words” by Extreme. Works every time.
Make something up on the spot and work her name into the lyrics.
If that doesn’t work, I suggest either Jeff Buckley’s “Your Flesh is so Nice” or Jimmy Kimmell’s “I’m F*$%ing Ben Affleck”, just to let her see the kind of twisted mind games she’s in for if she sticks around:D
Suzanne, by Leonard Cohen. Don’t do the whole song though, just the first verse and chorus. After that it gets weird. (Heros in the seaweed?)
Easy chords, easy lyrics, not too stalkerish. There’s always a lot of “well, aren’t we being romantic now and building our expectations” with songs that are directly about how much you love her. Singing a song about a girl named Suzanne might defuse some of this, and make it less spotlight-like.
My personal favorites:
Gilgarra Mountain - The family theme song, she turns him over to the guy he robbed for her, and he has to bust out of jail.
Black Velvet Band - All about being deported after a prostitute plays the singer for a patsy and leaving him holding the loot.
Dirty Old Town. “I met my love, by the gasworks wall”. Always makes Ms. Attack get all misty eyed. Or maybe that’s a glaze over.
If you’ve REALLY got guts, go with Polly Von, it’s all about killing your true love by accident while swan hunting. I hate it when that happens. Y’know, maybe you should stick with Suzanne.
I’m a woman, and any man who would play and sing The Beatles “And I Love Her” to me would have a very nice evening indeed.
If I could sing, I would play ‘Time in a Bottle’. Since I can’t, and prefer a blues shred, I would sing and jam ‘I’m the One’.
Mrs Made in Macau likes me to sing and play Steve Earle’s ‘Valentines Day’ - a song about forgetting that it’s Valentine’s Day. Love that song.
MiM
Does she already like you? :dubious: Because this probably won’t go over well if not.
I’ll have to say I love you in a song by the late great Jim Croce.
I’d put her on the guest list. But then she’d probably run off with the bass player, because he’s better looking than me.
"I gave my love a cherry which had no stone,
I gave my love a chicken which had no bone,
I gave my love a story which had no end…"
When I was a kid, learning guitar, my teacher said “Ya gotta learn Time in a Bottle – guaranteed to getcha laid.” I was shocked, since I was a kid, though I suppose I looked sixteen. Anyway, I learned the tune, but I couldn’t sing to save my life and never tried to profit from the song’s supposedly magical powers over women. I have no idea whether this song is well-known anymore or whether it’s mostly drifted into obscurity. Anyway, it seems a tad much to be singing to someone.
I would try to learn a really cheesy guitar version of that song Kramer and Newman were playing when they made sausages in Jerry’s kitchen. Dance around like an idiot while you play it. You’ll find out if she has a sense of humor, anyway.
Oh, I’m not the guy. I’m a girl. I’m just in the mood for discovering these kind of songs. You guys are being very helpful!
Sting’s *Fields Of Gold *is a classic in this genre.
Will you stay with me, will you be my love
Among the fields of barley
We’ll forget the sun in his jealous sky
As we lie in fields of gold
Lyrics