Hello Smudgey,
Aww... This is the kinda romantic thing FeowFeow likes to see
Ok, I'll help with some suggestions. For my guy's birthday, the
outing planned was based on what HE likes & usually wants to
do, but we didn't have the chance due to time constraints.
Activities
1. Does your bf like playing pool? If your dad has a country club
membership, bring him for a nice lunch there, & have a game of
pool.
2. Go to Pulau Ubin for a day out, pack insect repellent, a gourmet
picnic lunch & head out (I'm gonna drag my guy there 1 of these
days when we're Not so lazy 
).
3. Go to the museum, you will enjoy the Peranakan history, &
it's nice & quiet there during the afternoons.
4. Check 8 Days for any upcoming plays or open-air performances
that you & your guy may enjoy together (bring a lunch or night
picnic, depending on the performance).
Food
1. If you do decide to go to Pulau Ubin, or enjoy an open-air
performance such as Ballet Under The Stars, pack a pretty picnic
basket with big fat & delicious sandwiches, & a bottle of
wine (bring a wine chiller). From what I've seen, it's much neater
& classier than bringing lots of plastic bags & plastic
containers of laksa A great
place to get delicious sandwiches is Moomba Cafe (a personal
favourite of mine) behind Bank of China at Battery Road. They also
have boxes of mini sandwiches & cakes of different flavours for
you to try. They're absolutely delicious.
I'll leave the restaurants part to the other posters to give you
suggestions, as I'm sure they'll come up with better ones than I :
) I hope your bf has a great birthday, & with you taking time
& effort to plan it, I'm sure he will
FeowFeow
