50 Dating DOs and DON'Ts

by Glamour

Dating can lead to all kinds of tricky situations. To help you navigate even the most awkward moments, we've compiled our 50 best dating tips--some new, some old--given to us by experts, moms, women like you, and even Justin Timberlake.

1. DON'T look for perfection.
Encouraging you to settle isn't our style, but separating your desires from your deal-breakers can give your love life a major upgrade. "There are some qualities that your mate must have-being honest, for example--and others, such as movie-star looks, that should be thrown in the would-be-nice category," says Elizabeth R. Lombardo, Ph.D., author of A Happy You: Your Ultimate Prescription for Happiness. "Sit down and realistically figure out what characteristics are nonnegotiable and then be open-minded about the rest."

2. DO expect to meet men in unexpected places.
"Keep your eyes open at all times for opportunities to meet quality men, not just when you are all dressed up to go out," says dateologist Tracey Steinberg.

3. DON'T assume that somebody's not interested in you.
Don't conclude that if you don't think you look cute, you don't look cute to someone else, says Paula Bloom, author of Why Does He Do That? Why Does She Do That?.

"So if you're running to the grocery store after the gym, and some guy starts talking to you and trying to make conversation with you, you may be thinking he just wants to talk to you when he's actually really trying to make a connection with you. If you don't think you look attractive, you might miss it."

4. DO be confident and make the first move.
The jury is in: Men really do prefer women who make the first move. "It's not because it takes the pressure off of them," said Christopher Brya, coauthor of WTF Are Men Thinking. "Instead, it shows that you're confident, which is really the biggest turn-on." Many guys sense that the frequency of men making the first move (asking for phone numbers or dates, etc.) is actually diminishing. As one guy put it, "Waiting for a man to make the first move is real old-school and outdated." Plus, if you're a take-charge woman in every other facet of your life, why be a wallflower when it comes to men?

5. DO make it easy for men to date you.
True story: Guys have a fear of rejection. If you make it easy for them to ask you out, the more apt they'll be to do it. "Making it easy means telling a man in the clearest terms that you are interested and wouldn't say no to a date," says Harlan Cohen, author of Getting Naked: Five Steps to Finding the Love of Your Life (While Fully Clothed and Totally Sober).

6. DON'T go out in one huge group.
"The best size group to go out with is three," says Shannon Fox, the author of Last One Down the Aisle Wins. Going out alone might invite men to talk to you but only because you seem vulnerable and desperate. Two is too easily unbalanced. (What nice guy wants to ask a girl to dance if it means leaving her friend all alone?) And four is too intimidating-no guy wants to risk putting himself out there in front of a gang of potentially critical women."

7. DON'T worry about his age--or yours.
The times have changed, and age just isn't as relevant anymore when it comes to dating. Miguel Almaraz, coauthor of WTF Are Men Thinking?, said, "Younger men--20 to 30--really do like dating older women. In fact, 66 percent of the men we polled [for the book] said they would date older women." The main reason given? Experience.

8. DO put a friend in charge of finding you a date.
Not great at seeing who's good for you? Then stop trying and let a friend do it for you. Whitney Casey, author of The Man Plan, says to pick a (preferably coupled-up) close friend and put her in charge of finding guys--any other guy you meet automatically goes in the friend zone. "You'll only go on dates with someone she sets you up with," Casey says. Not only does this help you date better men, you'll also end up acting more genuinely around other guys you meet when the should-I-date-him pressure's off.

9. DON'T limit your online dating searches.
Doing the online dating thing? Make sure you cast a wide net. "Extend your search two inches in height below what you want and two years older and younger than what you think you are looking for," says Brenda Della Casa, author of Cinderella Was a Liar.

10. DON'T pretend to be someone you're not, even online.
Online dating is competitive, but being yourself is essential. "If you're pretending to be someone you're not, you're going to end up on a date with a person who is compatible with the person you're pretending to be, not the person you actually are," says Lisa Daily, author of How to Date Like a Grown-Up.

11. DO give people permission to want you and not want you.
OK, this might sound trite, but it really does make a lot of sense: "The Universal Rejection Truth of Dating and Relationships says that thousands of people will want to date you, but millions will not," says Cohen. "Until you can give people permission to not want you, it will be too hard to meet the people who do want you."

12. DON'T waste your time dating a show-off.
"The bravado? That guy needs to save it for the golf course."
--Justin Timberlake

13.DO be nice to everyone.
"I can't stress this enough," says Rachel DeAlto, author of Flirt Fearlessly: The A to Z Guide to Getting Your Flirt On: "You never know where an encounter is going to lead. That guy you met at the gym but aren't into? That woman you met at the networking event last night? They might be the one to introduce you to your dream guy."

14. DO tell a friend when you want to be more than friends.
"Unless you have only one friend and telling this friend means losing your only friend, it's not friendly to keep a friend from dating the best possible single person on the market--you," says Cohen.

15. DO go on a date with someone you feel so-so about.
If you haven't been on a date in a while, this could be the ideal opportunity to get back out there and practice. "I recommend meeting up with the guy for only an hour over coffee or one drink," says Smitten blogger Ariane Marder. "Because you're not invested, you really have nothing to lose--besides a precious hour of your time that could be spent trying to figure out why no one is asking you out. (Sigh.)"

16. DO allow yourself to be wooed.
"It feels good to be treated like a lady. If a guy really likes you, he'll pick you up and take you out, not ask you to drive across town for cocktails and a sleepover."
--Alison Brie, star of Mad Men and Community

17.DON'T plan a complicated date. Start with the basics.
It's tempting to be creative and plan a date that's fun and outside-the-box. But don't underestimate the value of the tried-and-true standards. Almaraz says, "While men like creative dates, they said they would prefer those types of dates later in a relationship." Sixty-two percent of men polled for his WTF Are Men Thinking? book said they prefer dinner or a movie for a first date. One even said, "Dinner is always good as long as it's relatively casual. I think going too fancy on a first date can reek of desperation to impress. You're there to get to know the other person, not to get involved in activities that present opportunities to ignore each other."

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18. DO let go of the day's frustrations before a first date.
"When chatting about your day, it may seem natural to bring up the bad day you had at work, the argument with your friend, or the fact that you couldn't find parking earlier," says James Wadley, Ph.D., the author of Would You Marry You? But on a first date, you might want to "keep your bad attitude at home, and then go out to meet others to show them how adaptable, resilient, and sexy you can be."

19. DON'T go overboard on dressing sexy.
Sure, you want to look hot on a date (we've got you covered with tons of outfits guys love), but don't go overboard. "On dates and when out trying to get dates, I recommend dressing about 20 to 30 percent sexy," says Steinberg. "Give him a little something for his imagination."

20. DO wear shoes that are comfortable.
We love our pointy-toe stilettos too, but if you're seeing someone new, maybe go brogue instead. "Some of the best dates are the ones that continue going on beyond what's planned," says Bloom. "You're improvising, and you don't want uncomfortable shoes to be the reason you cut short a date that's going well."

21. DON'T booze it up with a new guy.
"Imagine you have two brains. One weighs risks and rewards, keeps you informed about morals and ethics, and warns you about unwise choices. The other seeks pleasure and feel-good experiences, creates erotic appetite, and drives you to satisfy that appetite," says Brian Alexander, coauthor of The Chemistry Between Us. "As anybody who's been on a diet and has faced down a plate of gooey chocolate chip cookies can tell you, it can be pretty tough to resist pleasure under normal circumstances, but when you drink alcohol, you are helping to cripple your rational, reasoning brain and giving your pleasure-seeking brain a huge megaphone. So, let's say you're out with a guy. He's cute, but you're feeling just so-so about him and you probably wouldn't want to go out with him again. But to make the date a little more fun, you start in on the martinis. Soon all you can see is the cute. A few hours later, you're looking at a very awkward morning."

22. DO learn to really listen to the man sitting across from you on a date.
"He is telling you all you need to know those first few times you get together. Really tune in when he drones on like a mama's boy or blabs incessantly about his ex. If he's unavailable--married, moody, or obsessed with his motorcycle--toodles to him. Really hear what he's sayin' right off the bat, ladies, and you'll save yourself a whole lot of heartache down the road." --Maryjane Fahey and Caryn Beth Rosenthal, authors of Dumped

23. DON'T treat dates like performance art.
Remember, you're not only trying to impress the guy; you should be seeing if he's a good fit for you. "I tend to forget that and treat dates like I'm on a stage in front of an audience of one," says Smitten blogger Gena Kaufman. "I plan my wardrobe for hours, perfect my makeup, and once at the bar, it's show time: jokes, stories, hair flips, etc. If a guy seems charmed by my act, I consider it a good date. But then flash forward to a third or fourth date, when I realize that while I was so busy being excited that he liked me, I forgot to actually notice whether I was interested in him."

24. DO flirt.
"Make eye contact and smile at anyone who catches your eye for three seconds," says DeAlto. "If he is interested, he will approach. In a relationship? Keep flirting! Continue to make him feel like the center of the universe. It will do wonders for your connection."

25.DON'T forget your manners.
We can't imagine this is something you'd ever do, but a little reminder never hurts: Say thank you.
"Good manners have become so old-fashioned that men now wait for the thank-you at the end of the date as a way to see if she's worth seeing again," says Brian from New York City. "I don't care if the woman looks like Kate Beckinsale and has a Ph.D.; if she can't be bothered to utter those two little words, I am never calling her again."

26.DO order what you really want.
"Don't be afraid to eat like a man. A guy would love to see a woman with a healthy appetite."
-Michael Urie, star of Partners

27. DO pay attention.
Guys notice when you're interested in what they're saying, so make sure he's got your full attention. "Give him direct eye contact about 80 percent of the conversation, be positive, and smile easily," says Steinberg. "A group of wild coyotes could break down the door, but you would be too enthralled to notice!"

28. DON'T ask the "five-year plan" question too soon.
"Talking about at what age you'd like to get married and have kids too early in the conversation changes the whole tone of trying to get to know someone," says Jessi Bockting from Louisville, Kentucky. "It suddenly feels like a job interview."

29. DO look for red flags.
"People have a great way of telling you who they are, if you are willing to listen," says Della Casa. "I once knew a woman who went on a date with a guy who jokingly told her he lacked empathy. She brushed it off and wondered why he was so callous with her feelings six months later. If the guy you are dating makes questionable comments, is rude to the waiter, or otherwise sends your gut into a spin, move on."

30. DON'T let him know you've been Google-stalking him all week.
"Look, we know that you've been investigating this guy online since you learned his last name. (We don't blame you, and chances are he's done the same to you.) But if you start in on his alma mater, favorite bands, and how his hair looked in 2004 (which was found thanks to your mad skills at image searching), you are going to creep him out. Big-time."
--Daniel Holloway and Dorothy Robinson, authors of Dating Makes You Want to Die (but You Have to Do It Anyway)

31. DO casually touch him.
"The way to a man's (or a woman's, for that matter) heart isn't through his stomach, but his eyes," says Alexander. "Humans have evolved to read the emotions of others, and one way we do it is by looking into the eyes. When we touch each other, even with a casual arm stroke or a friendly hug, and look into each other's eyes, we can trigger a series of chemical events in the brain that lead us to open ourselves up to another person. A hormone called oxytocin is released, driving this response. That's followed by dopamine, a chemical that motivates us to seek out rewarding experiences, like being with you."

32. DON'T talk about your ex.
"No good can come of this! You'll seem either bitter, heartless, or still hung-up--and any one of these is a huge turnoff."
--Em and Lo, emandlo.com

33. DON'T apologize for being who you are.
"Why waste valuable cocktail time with your pals with some wuss who can't handle you. Screw anyone who has a problem with that--no discussion!"
--Maryjane Fahey and Caryn Beth Rosenthal, authors of Dumped

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34. DO be aware of time.
"When you're on a date, one of the ways to know it's going well--if you guys are connecting--is, as the date's wrapping up, if you're thinking Where did the time go? versus Oh my God, I'm so glad this is over," says Bloom.

35. DO read into the first kiss.
It may seem like dating 101, but a kiss at the end of the evening really does shed light on how he feels. "This may sound hard to believe, but a whopping 74 percent of guys [polled in WTF Are Men Thinking?] would not kiss their date at the end if they were not attracted to her," says Almaraz. "If you're on the date and you like the guy, lean in for that kiss. If he's into you, you'll know quickly."

36.DO play it straight.
"Honesty, with yourself and the person you're dating, is always the best policy," says Alexander. "I don't just mean telling the truth about what you do, or that you're not really that great a skier, but also honesty about what you want. Any man worth your time will appreciate a woman who has reasonable expectations for him--and him for you. Also be honest about what you want from life. Conforming to what you think he wants isn't a great recipe for anybody."

37. DO accept that a date is not a relationship.
Remember that most dates are nights out with strangers--even if you've gone on three of them. "It's OK to be excited, but take some time to get to know the person in front of you before you plan your future together in your head," says Della Casa.

38. DON'T be a friend with benefits if you want a relationship.
"If you want to date someone, do not pretend you are OK just having sex," says Cohen. "If you've started and want to know if someone wants to be with you or just your vagina, stop offering the benefit until you can get a commitment."

39. DON'T expect anything if you sleep with him.
"If you want to sleep with him, go ahead--just be safe!--but understand that most men have a remarkable ability to separate sex and emotion," says Della Casa. "If he's not calling you his girlfriend, taking you to dinner, or otherwise courting you beforehand, don't expect a roll in the sack to change that."

40. DON'T overanalyze or investigate if the guy doesn't call you again.
"You two didn't click. So what? Move on and don't take it personally. Don't cloud yourself up with negative thoughts--it'll just drive you nuts, and you know it."
--Maryjane Fahey and Caryn Beth Rosenthal, authors of Dumped

41. DO date at your own pace.
"My mom told me that I should never compare my relationship with my friends' relationships. About five of my girlfriends got engaged within six months of one another, and I started wondering what was wrong with me. Was it OK that I didn't feel ready to marry my boyfriend of two years? Did that mean I didn't really love him? My mom said, 'You can't put yourself--or the relationship--on a time line because of the way another relationship has progressed.'"
--Kaci Eaves, Fort Worth, Tex.

42. DON'T talk yourself into a relationship.
"If it doesn't feel right, then it's wrong," says Cohen. "Relationships shouldn't be complicated, and it shouldn't take convincing yourself someone is good enough for you."

43. DO stop asking for love advice.
"When you ask for 20 people's advice on what to do in a particular situation, you can become paralyzed by information overload and end up going against your best judgment," says Daily. "Just go to one or two close friends when you need a hint in the love department. Or even ask yourself if you need advice at all--most of the time you probably already know what to do."

44. DO remember that you're the object of your affection.
"I take myself out, treat myself to massages, and am making a conscious effort to be my own beloved," says Marder. "When I feel down, I think about what I would say to someone I care about and do the same for myself. I figure as long as I'm living single, I may as well make it worth it."

45. DON'T text.
"Communicating by text doesn't trigger the same responses in our brains as interacting face-to-face," says Alexander. "Texting is less rewarding and provides less of the chemical reactions that lead to human bonding. It's not like you shouldn't ever text, like if you're late or want to change plans, but if you've got anything important to say, including something seductive, texting isn't the way to go."

46. DO trust your instincts.
"Years ago, I suspected that my boyfriend was cheating. I even went looking through his phone for proof. The thing is, guilty or innocent, it didn't matter. I already knew in my gut that he was wrong for me. Now I listen to my gut and save myself the detective work."
--Genese Jamilah, Savannah

47. DON'T waste time being jealous.
"That guy your best friend just got engaged to was right for her, not you, and her engaged status doesn't mean you will always be single," says Della Casa. "Be happy for your friends and not only will your friendships flourish, but you may even meet someone at their weddings."

48. DO your best to listen to your friends when they tell you your new boyfriend is a douchebag.
"When the people who love you the most have a problem with someone who knows you the least, listen up," says Cohen. "These people probably see something you are too afraid to see or want to avoid acknowledging."

49. DO stay positive.
"Even if you have had a few frustrating experiences, a great attitude will make all the difference," says DeAlto.

50. DO have a life outside your relationship.
"You never know, one day your boyfriend or girlfriend might say goodbye," says Cohen, "and if you always have a life, you always have somewhere to go, something to do, and someone to go with."

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