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You’ve finally summoned up the courage to address that beautiful women you’ve been admiring every morning on your commute as she sits across from you, sipping coffee and reading AM New York. She’s agreed to meet you for drinks after work, so now you all you have to do is not blow it by coming off like a shallow asshole.

You can do this by making sure your first date compliments ring true, rather than simply coming off like lines to get her straight to the bedroom. Since we’re assuming that you truly do want to get to know this intriguing woman you’ve invited to the bar, here are some ways to avoid getting tongue-tied and blurting out ridiculous stock compliments that compare her eyeballs to whirlpools:

1. If you’re going for a physical compliment, make sure to focus on the face (but avoid the eyes).

“Boy do you have great breasts” does not constitute the most respectful ice breaker. If you want to convince this woman that you care for nothing other than the potential to get laid, go ahead and extol the virtues of her behind or her legs. Otherwise, pick a facial feature that genuinely stands out to you. If they happen to be her eyes, even though that over-used compliment can be seen as extremely cliche, you’ll probably be forgiven.

2. Being a tad self-deprecating can’t hurt.

Admitting that you were a bit shocked and totally thrilled that a woman like her would agree to go on a date with a guy like you will usually receive a warm smile from the woman in question. It shows that you appreciate her and her time from the get-go. If you’re a male model, on the other hand, save this one for the nerdier guys out there, okay?

3. Tell her why you decided to ask her out, and make sure that reason doesn’t center on her looks.

Maybe you’ve always wondered what she’s focusing so hard on while she squints at her Kindle on the train into the city each morning. You figured she had interesting thoughts, or noticed that her reading choices always appealed to you. Perhaps she wears dresses with wild patterns that you were certain highlighted her personal creativity. Whatever it is, there was something about her that caught your eye, and you shouldn’t hesitate to tell her.

4. Admit that you’ve been looking forward to your date since you invited her to dinner.

Go even further to attest that it’s been living up to your expectations (which you implied were high, based on your anticipation). As long as you can avoid being creepy about this and can make her laugh when you say she’s just as fun to hang out with as you had hoped, you’re golden.

5. Take a complimentary interest in her hobbies without pretending to share them.

Though your first instinct may be to try and relate as much as possible to the woman you’re just getting to know, you must resist the urge to pretend you also love quilting (or skiing, or fishing, or whatever hobby she professes to enjoy most). It will sound disingenuous, and if things go well, she’ll quickly catch you in your lie. However, complimenting the fact that she’s passionate about something communicates that you like interesting women, which (I don’t think I need to explain) is a good thing.

6. Don’t be afraid to notice the details guys usually take for granted, like her shoes.

If you notice that a woman took some time to get ready for an evening out, it’s definitely okay to acknowledge her work by noting how you love the color of her nail polish, or by saying that her dress looks really pretty. Sometimes, men fear that this will make them appear “gay.” Besides that being an offensive thing to worry about, it’s ridiculous–you asked this woman out a date, remember?

7. When the date’s over, say you had fun without going overboard.

There’s no need to exaggerate and declare that your one-hour dinner constituted the most amazing date you’ve ever been on in your life. Just relax and tell the lady you had a great time. This, in and of itself, is the compliment that will ultimately lead you to date number two.

Photo copyright: Phase4Studios/Shutterstock

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