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Q. I’m writing on behalf of my younger brother, who, l believe, would never consider submitting  a question himself.  He’s begun approaching women, and I was horrified to overhear him use a cheesy pick-up line recently—any suggestions?  I have no idea how he’s coming up with these lines.  I’m not sure he’ll listen to his big sister, but I have to try something!

A.Your brother’s lucky to have a sister who can give him the inside scoop as to a woman’s point of view.  Consider positioning it that way, and letting him know that women are far more likely to be receptive to any of the following four approaches than cheesy pick-up lines.

1. Is This Seat Taken?
This line tends to work because it doesn’t automatically come across as a pick-up line. Instead, it’s seen as a respectful gesture. After all, you don’t want to assume that a person sitting next to an empty seat is at the venue alone. By asking if the seat is taken, you’re acknowledging that while also opening up the opportunity for conversation. If the seat is taken, you might consider asking, “By whom?” to get a feel for whether or not the person is there with a significant other or just a friend.

2. I Really Like That ____
Another effective way to strike up a conversation with somebody is to pay them a respectful and sincere compliment.

Notice: The key to a lot of these pick-up lines is respect. Maybe the girl he’s been eyeing is wearing a really nice necklace. By pointing this out, he can start the conversation off on the right foot.

3. Could I Get You Another Drink?
If he’s at a lounge, concert or other place that serves drinks, he might consider taking note of what a woman is drinking and asking if she would like another after finishing it.

It’s best to wait a few minutes after the woman has finished her drink to approach, because you don’t want the person to assume you’re just trying to get her drunk. However, offering to buy another drink shows that you’re trying to be polite and that you’re attentive enough to notice what the person was drinking.

4. Will You Help Me With This?
Asking a potential love interest to help you with something—something simple, of course—can be a great way to kick things off. For example, your brother could ask that cute girl at the next table if she knows the name of the song that’s playing. By opening up a conversation this way, you show the person that you value her opinion.

What better way to get things off on the right foot?

Jasbina is the founder and president of Intersections Match, the only personalized matchmaking and dating coaching firm serving singles of South Asian descent in the United States. She is also the host of Intersections Talk Radio.

Jasbina Ahluwalia

Jasbina Ahluwalia adds a unique contribution to the Matchmaking industry–she has pioneered an approach to matchmaking, which blends the best of the East and the West. She is an Indian-American attorney-turned-entrepreneur,...