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What you can do, is making sure both of them are on a good mood. The best way to get the romance going, is giving the other sim a romantic gift. Sims tend to like most gifts, so just buy something from the gift catalog on your phone (books tend to go over well) and giving it first before trying any romantic interactions. Romantic gifts, if successful, make both of the sims gain the "Flirty" moodlet, and flirting is ten times easier if both sims are flirty. There's also a kind of scoring system when it comes to the interactions, so you want to do low level flirty interactions first. Things like "Flirt" and "Blow a Kiss" are low level, while "Ask Risque question" is quite high level, meaning you shouldn't mess with it if both sims aren't very flirty. Then there's the conversation tone, the best one for flirty interactions is "amorous conversation", and the best help for this is again, romantic gift. I'm 90% sure a successful romantic gift turns the conversation immediatelly into an amorous one. It makes flirty interactions more successfull.
It's the age-old adage, "Slow and steady wins the race"
Start with minor romance tasks like @Marinuttonen mentioned. Only Flirt at first. MAYBE compliment looks... nothing more than that for a while. It helps to have friendship up high. If friendship is low, then forget romance. Work on getting friendship up first.
There are tricks and exploits you can make use of if you REALLY can't get it done. Quite a few of them actually... The biggest ones...
* Get a romance bucket. The award from getting gold on a date. Enable the emotional aura and instant flirty.
* Paint a flirty painting and enable it.
* Use the fashion photographer studio to take a picture of a flirty sim. The photo will have the "Flirty" buff when enabled.
* Create yourself a "Home" club. Basically a club with all home activities, leave it running all the time until you get tons of points, then put points in all the Flirty bonuses.
* There's a flirty NAP in ECO Lifestyles. (I wouldn't recommend that one, NAPs are all horribly broken)
* Lot traits, Create a sexy nightclub and give it one of the romance lot traits. Take your sims there.
* Aren't there "flirty" cookies?
* Flirty TV shows, books, Valentines day... etc etc
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