Your Best Friend’s Sister
Why you shouldn’t: “Blood is thicker than water,” says Siski Green, author of How to Blow Her Mind in Bed. “You’re risking a relationship that has been built up over years for one that might not last.”

Why you should: “You have a lot in common, which is a strong basis for a relationship,” says Dr Pam Spurr, author of Fabulous Foreplay. “If she’s younger, she’s quite possibly had a crush on you too.” That’s what’s known in the trade as an “in”.

The next move: “Prep your friend by mentioning a recent pay rise,” says Green. “Indiana State University research found family members have a massive influence on women’s choices, and male family members want her to date a good provider. A male family member would rather she didn’t date anyone, but you can become his next best option. Calm his over-protective instincts by not being too touchy-feely when he’s around.”

Your Child’s Teacher
Why you shouldn’t: “Parent-teacher meetings are awkward enough without come-to-bed eyes across the table,” says Kate Taylor, author of Not Tonight, Mr Right. “She’s a big influence in your child’s life. If you screw up, will junior suffer?”

Why you should: “If you’re a single parent, new people are hard to meet and you already have common ground,” says Spurr. “Plus, she likes children.” Well, you’d hope anyway.

The next move: “You probably have a three-minute slot to make an impression, so apply speed-dating tactics,” says Green. “Make eye contact, mention you’re taking your child for pizza and ask what her favourite topping is. This open-ended question will draw her into conversation and she’ll feel she has disclosed private information to you. Harvard psychologist Dr Zick Rubin found eye contact and disclosing personal info are key to making someone fall for you.”

The Work Experience Girl
Why you shouldn’t: Think Lewinsky. Dribbling over 22-year-olds marks you as the office letch. You’ll lose the respect of colleagues and blow your chances with other women.

Why you should: “You’re pursuing the same career, so you have plenty in common,” says Taylor. “As soon as she’s packed up her desk, you’ve got the green light.” As long as she’s not off to do her GCSEs.

The next move: “Asking her out should be the easy bit – women are wired to be attracted to high earners, and if she’s prepared to work for free, she’s probably ambitious,” says Green. “Ask her out for a drink on the pretext of giving her some career pointers.” If it progresses, dodge the Stringfellow jibes by getting it out in the open. “A study in the Duke Journal of Gender Law & Policy showed men who enter workplace relationships because they have authentic romantic rather than lustful feelings generate positive office gossip,” says Green. “Tell the office hyenas you have a ‘genuine connection’.”

The Girl Your Buddy’s After
Why you shouldn’t: “There’s no bigger blow to a man’s ego than to be rejected in favour of his friend,” warns Taylor.

Why you should: “You’ve got the same tastes in music, films and friends as your buddy, and this inevitably extends to women to a certain degree,” says Green.

The next move: “Don’t make it into a competition,” warns Green. “Instead, set him up with someone else. His attraction for the other girl will decrease as his oxytocin levels starts to rise in reaction to the new girl.”

Your Boss’ Daughter
Why you shouldn’t: He holds your financial testicles in his hands. Averted eyes over breakfast may not up your chances of a promotion.

Why you should: She’s out of bounds, so while most people will look, very few will touch. “She is very powerful by association and power is a mighty aphrodisiac,” says Green. “This means most men will be too scared to approach her, so the field is clear and she may be grateful for your confident advances.”

The next move: “Two of the main traits women find attractive are power and self-confidence,” says Spurr. “A man who takes risks exudes power and you can score big just by making a mature, confident approach. Don’t do to great lengths to impress her – if you’d take a first date to a burger bar, take her there. The key is not to be in awe of her status, which will allow her to relax and enjoy herself.”

From September 2008 issue of Men's Health Singapore