The key to delivering a compliment to a woman without it becoming awkward is to deliver a genuine compliment that you actually mean. Complimenting a woman for the mere sake of complimenting her will sound disingenuous and leave the woman wondering why you bothered.
A True Compliment
If you give compliment because you truly mean it - and not because you're just trying to flatter the woman - it's far less likely to be awkward. Strive to give genuine compliments that focus on attributes she controls.
Avoiding Inappropriate Compliments
Any time you compliment a woman on her physical attributes, there's a chance it can fall into the realm of inappropriate. This is especially true in a setting where you have any form of power or influence over her position. For example, an academic advisor telling a female student that she has "great legs" is inappropriate because the advisor is in a position to potentially damage the student's academic career. On the other hand, telling her that she has "scholarly inquisitiveness" is a completely appropriate compliment within this relationship.
Avoiding Rude Compliments
Any time a compliment may seem like a veiled attempt at control or minimizing the woman's place in society, it falls into the realm of rude. For example, telling her she's "surprisingly strong" or "strong for a girl" when she picks up a heavy box isn't a compliment - it's an attempt to remind her that she's supposed to be weak. Telling her instead that she's simply "strong" is an appropriate compliment.
What do you admire about the woman? If you've had hours of brilliant, mind-blowing conversations that demonstrate her unparalleled intellect and quick wit but then turn around and say something like, "I sure like spending time with you because you're so easy on the eyes," you've just reduced your interactions down to nothing important. What she once thought was an intellectual exchange between contemporaries now feels like a ruse; she'll wonder if you pretended to be intrigued by her only because you think she's attractive. So when she subsequently acts awkward around you, it's not because of your compliment - it's because of what the compliment meant.
Avoid an awkward situation by making your compliment a statement instead of a question. For example, asking, "Has anyone ever told you that you have beautiful eyes?" may result in an awkward pause, followed by her reply of, "Uh...yes." It's far better to just state the compliment: "You have beautiful eyes."
Compliment Her Efforts
Instead of complimenting things that take no effort on her part (such as things that are genetic and she was born with), compliment her on accomplishments. For example, if she's working toward being more fit, compliment her increased muscle tone instead of specifically pointing out how firm her backside looks.
Complimenting women you don't know can be tricky since you don't know how it will be received. It's fine to tell a woman who you don't know that she has a great jacket or even a great smile, but it's not fine to tell a female stranger that she has a "banging body."
Your Body Language
The way you deliver the compliment and your body language can have a huge impact on how it is perceived by the recipient. Here are some tips on not sounding awkward or creepy when complimenting a woman:
- Don't physically close her off from other people as if she has no means of escape.
- Don't pair the compliment with physical touch unless you two have that type of familiarity already.
- Make eye contact, but not so much so that it seems aggressive.
- Smile and don't close off your body by crossing your arms.
A genuine compliment which is not meant to entice a woman or make her like you, is less likely to be awkward. Analyze your reasons for giving the compliment; are you romantically interested in her? If so, take a step back and think about what you can say to her that is complimentary and not an attempt at influencing her thoughts of you. A true compliment should be a gift that requires no payback.