Her Best Friend

The fear:

You’re another jerk. She’ll notice immediately if you have anything in common with previous jerks. She may be stand-offish at first, warns LaDawn Black, author of Let’s Get It On: 15 Hot Tips and Tricks To Spice Up Your Sex Life.

Your plan:

Work on befriending her, but be genuine, says Black. Take an interest in her problems. Offer thoughtful, honest opinions. Listen when the two gal pals talk about boyfriends past. “You’ll be able to fifind out what the other men did wrong,” says Leil Lowndes, author of How To Talk To Anyone.

Her Friendly Ex

The fear:

He’ll be shut out. Lunch and coffee dates that were once his domain will be ceded to you, sparking his fear that he’ll be totally forgotten.

Your plan:

Her ability to have a friendship with a former flame shows that she’s mature, so don’t act suspicious – you’ll look insecure. “Make him feel as if he’s part of her life without always inviting him along,” Black says. Example: giving him a shout-out when they’re on the phone together can let them both know you don’t feel threatened.

Her Cat

The fear:

You hate cats. While Mr Whiskers (we hope) has no say in the relationship, don’t think she won’t notice if the cat runs the other way when you come over. “Most animal lovers, especially women, see their pets almost as children, so if you don’t share her love, it can be difficult for the relationship to move forward,” says Susan Logan, editor of Cat Fancy magazine.

Your plan:

Let the animal sniff you, then scratch it under the chin or behind the ears. Ask your lady to let you feed the cat to help it form a positive association – you visit, kitty eats!

Her Mother

The fear:

You’ll hook her little girl and then hit the road.

Your plan:

If her parents are still together, ask her mother how they celebrated their twenty-fifth anniversary or what they’re planning for their next. It shows you’re not a commitment-phobic cad, Black says. If your girl’s birthday is coming up, involve her mom in the planning. You’re thoughtful, is the right message to be sending.

Her Father

The fear:

You won’t be able to give his daughter the life she deserves. Even if she has her own career, “most fathers still want to know that their daughters will be taken care of,” Lowndes says.

Your plan:

Don’t talk salary – it screams insecurity. Instead, ask his opinion on a financial matter, such as the stocks he’s been following. Aside from flattering him, you’ll make it clear that you’re a financially responsible person planning for the future.