Curious to hear what women thought about their online dating experiences, we asked them… and were floored by their responses. We heard it all, like, “A guy told me he was looking for a girlfriend by next year so he’d have someone to split rent with.” Then there was the charmer who told his date about the time he “got wasted, peed, and mopped it up with his clothes, and then wore them.” Um, yeah.
But we’d like to assume you know better than to make mistakes like these. Still, navigating the world of online dating can definitely be tricky—what kind of message is clever, but not creepy? What the hell are you supposed to say about yourself in your profile? When do you go in for the kill and ask for a date?
Here are a few common scenarios you might encounter in your online dating adventures. Here’s how—and how not—to best handle each situation.
The Dos and Don’ts of Online Dating
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Oliver Byunggyu Woo / EyeEm
Out of Town—and Out of Touch
The scenario: “A guy sent me a message saying that he wanted to meet up for a drink, but when I asked when he was free, he said he was ‘going out of town’ for the next two weeks and that we should schedule something after.” — Andrea, 31The problem…and the solution:If you tell a girl you’re “going out of town,” she’s going to assume you’re busy dating other women. By the time your date comes around, she’ll already have lost interest or have found someone more attentive. If you really are going away, wait until you get back to ask her out. A good rule of thumb: if you aren’t available for a date within seven days of sending the message, don’t send it.
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JGI/Jamie Grill
Not-So-Smooth Operator
The scenario: “I recently received a message that said, ‘Damn you’re a pretty white girl, you into muscular black men?’” — Kristen, 27The problem…and the solution: Aside from the obvious inappropriate nature of the comment to a complete stranger, men should never mention their physical characteristics or their own body parts in an introductory message. Women are easily scared away online, so you should avoid saying anything remotely controversial or predatory. Stick to neutral subjects—like mentioning a common ground you share based on something you read in her profile.
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Imperia Staffieri
The Insecure Online Dater
The scenario: “It’s so annoying and a major turn-off whenever a guy has something in his profile like ‘still not sure about online dating but…’” — Randi, 25The problem…and the solution: We get it. A lot of people are self-conscious about the fact that they’re on a dating site. But obviously if she’s on the site too, you’re both in the same boat. By pointing out your hesitations, she’s bound to assume you’re an insecure person. Just don’t bring it up. If you feel so inclined to explain yourself, wait to do it when you’ve met in person—and be confident about your reasons for joining.
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Maskot
The Gambler
The scenario: “I got a message that said, ‘Obviously you’re cute, but I’m just having trouble believing that this is actually you because you seem too good to be true. My buddy thinks you’re real and now we have a $20 bet going. Am I about to lose 20 bucks?” — Kristin, 26
The problem…and the solution: Aside from the fact that this is a pathetic pickup line, it’s certainly never going to work. A lot of women are looking for something serious and have no interest in participating in your immature wager with friends. Flattery is fine, but not to this degree. Try telling her she has a nice smile instead.
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PeopleImages
Dumped and in Denial
The scenario: “I went on a few dates with a guy I met online, and I eventually decided we weren’t compatible, so I was honest with him. He refused to accept it and continued to message me listing all the reasons why we’d be great together.” — Ashley, 30The problem…and the solution: No matter how strongly you feel about your potential with a woman you meet online, accept a break-up gracefully. There’s obviously a reason she didn’t think it would work out, so why keep trying to pursue someone who is clearly not interested in you? Instead, channel your energy into meeting someone else.
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Hero Images
Missing in Action
The scenario: “One time I was messaging back and forth with a guy for two weeks and having a great conversation, but he was taking too long to ask me out, so I stopped talking to him.” — Kelly, 32The problem…and the solution: If you’re into her, ask her out! What are you waiting for? And if you’re not, why are you still talking to her? Know that saying, “shit or get off the pot?” It applies here. A general rule: once you’ve sent four messages back and forth, someone should ask someone out. If not, that means it’s time to move on.
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Martin Novak
Pressure Cooker
The scenario: “I was really into someone I went on a few dates with, until he told me he was taking down his online dating profile and he wanted me to do the same.” — Jess, 34The problem…and the solution: Nothing will scare a girl faster than putting that kind of pressure on her too early into the relationship. When she’s ready to make her exit from the online dating world, she’ll let you know. Or if you feel compelled to bring it up, say something like, “I’m not interested in meeting anyone else online. I’ve been thinking about taking my profile down. What do you think?”
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NicolasMcComber
Generic Junkie
The scenario: “I can’t stand when I get a message that says ‘any fun weekend plans?’ That’s really all they want to know about me?” — Laura, 27The problem…and the solution: Sending a generic message—especially one as uninteresting as this—is not what’s going to make you stand out from other guys. Trust us, she’s getting a boatload of uninspiring messages like, “Hi, how are you?” and, “You’re gorgeous, I’d love to chat.” If you want to get her attention, try doing something a bit more personal. One girl we spoke to told a story about a guy who sent her a hilarious quote from a movie she had mentioned in her profile. Pick something specific she wrote about herself, and ask her a follow-up about it. If nothing else, she’ll admire the fact that you took the time to get to know her.
The scenario: “A guy sent me a message saying that he wanted to meet up for a drink, but when I asked when he was free, he said he was ‘going out of town’ for the next two weeks and that we should schedule something after.” — Andrea, 31
The problem…and the solution:If you tell a girl you’re “going out of town,” she’s going to assume you’re busy dating other women. By the time your date comes around, she’ll already have lost interest or have found someone more attentive. If you really are going away, wait until you get back to ask her out. A good rule of thumb: if you aren’t available for a date within seven days of sending the message, don’t send it.
Not-So-Smooth Operator
The scenario: “I recently received a message that said, ‘Damn you’re a pretty white girl, you into muscular black men?’” — Kristen, 27
The problem…and the solution: Aside from the obvious inappropriate nature of the comment to a complete stranger, men should never mention their physical characteristics or their own body parts in an introductory message. Women are easily scared away online, so you should avoid saying anything remotely controversial or predatory. Stick to neutral subjects—like mentioning a common ground you share based on something you read in her profile.
The Insecure Online Dater
The scenario: “It’s so annoying and a major turn-off whenever a guy has something in his profile like ‘still not sure about online dating but…’” — Randi, 25
The problem…and the solution: We get it. A lot of people are self-conscious about the fact that they’re on a dating site. But obviously if she’s on the site too, you’re both in the same boat. By pointing out your hesitations, she’s bound to assume you’re an insecure person. Just don’t bring it up. If you feel so inclined to explain yourself, wait to do it when you’ve met in person—and be confident about your reasons for joining.
The Gambler
The scenario: “I got a message that said, ‘Obviously you’re cute, but I’m just having trouble believing that this is actually you because you seem too good to be true. My buddy thinks you’re real and now we have a $20 bet going. Am I about to lose 20 bucks?” — Kristin, 26
The problem…and the solution: Aside from the fact that this is a pathetic pickup line, it’s certainly never going to work. A lot of women are looking for something serious and have no interest in participating in your immature wager with friends. Flattery is fine, but not to this degree. Try telling her she has a nice smile instead.
Dumped and in Denial
The scenario: “I went on a few dates with a guy I met online, and I eventually decided we weren’t compatible, so I was honest with him. He refused to accept it and continued to message me listing all the reasons why we’d be great together.” — Ashley, 30
The problem…and the solution: No matter how strongly you feel about your potential with a woman you meet online, accept a break-up gracefully. There’s obviously a reason she didn’t think it would work out, so why keep trying to pursue someone who is clearly not interested in you? Instead, channel your energy into meeting someone else.
Missing in Action
The scenario: “One time I was messaging back and forth with a guy for two weeks and having a great conversation, but he was taking too long to ask me out, so I stopped talking to him.” — Kelly, 32
The problem…and the solution: If you’re into her, ask her out! What are you waiting for? And if you’re not, why are you still talking to her? Know that saying, “shit or get off the pot?” It applies here. A general rule: once you’ve sent four messages back and forth, someone should ask someone out. If not, that means it’s time to move on.
Pressure Cooker
The scenario: “I was really into someone I went on a few dates with, until he told me he was taking down his online dating profile and he wanted me to do the same.” — Jess, 34
The problem…and the solution: Nothing will scare a girl faster than putting that kind of pressure on her too early into the relationship. When she’s ready to make her exit from the online dating world, she’ll let you know. Or if you feel compelled to bring it up, say something like, “I’m not interested in meeting anyone else online. I’ve been thinking about taking my profile down. What do you think?”
Generic Junkie
The scenario: “I can’t stand when I get a message that says ‘any fun weekend plans?’ That’s really all they want to know about me?” — Laura, 27
The problem…and the solution: Sending a generic message—especially one as uninteresting as this—is not what’s going to make you stand out from other guys. Trust us, she’s getting a boatload of uninspiring messages like, “Hi, how are you?” and, “You’re gorgeous, I’d love to chat.” If you want to get her attention, try doing something a bit more personal. One girl we spoke to told a story about a guy who sent her a hilarious quote from a movie she had mentioned in her profile. Pick something specific she wrote about herself, and ask her a follow-up about it. If nothing else, she’ll admire the fact that you took the time to get to know her.
