(The Frisky) -- Dear Wendy:
I'm a guy who has been dating online for a year and a half with very limited success. Aside from one two-month relationship, the process has been a total failure. I'm an only child from a family that never talked about sex or dating, so it's no surprise that romance is the only area of my life in which I'm painfully shy.
In fact, most of what I've learned about "what women want" is from female friends who tell me about getting hit on by creepy guys. As a result, I'm overcautious about compliments and physical contact to avoid being one of those creeps.
Second dates aren't any better, and by then even I know that I'm coming off as cold. So, Wendy, how much complimenting should a guy do on a first date? How do you casually touch on a first date, or is that creepy? Do women expect a goodnight kiss after a first online date (assuming it went well), or is a friendly hug the standard until date number two?
I know that I can't read my dates' minds, but nobody taught me the basic etiquette and I feel like I've been very withdrawn as a result. Heck, I've avoided asking girls out again because I'm so afraid of getting slapped for trying to kiss them at the end!
-- Walking on Eggshells
Dear Walking on Eggshells:
First of all, it might help you to remember -- or realize, if it's something you hadn't considered before -- that those women you've been going out with are probably just as nervous as you are, if not more so.
Dating is kind of scary in general, particularly the online variety where every first date is, for all intents and purposes, a blind one. Not only do you worry about whether the person you're meeting up with lives up to your expectations or the way she represented herself online, you have to worry about how you live up to her expectations.
And then there's the conversation and wondering what topics are appropriate and what you should avoid talking about.
Should you ask her about her dating history? (No.) Admit you're recently divorced? (Only if she asks.) Is it too boring to talk about work? (No, but keep it short.) Will she think you're being too forward if you tell her you like her dress? (No, but there are probably better ways to compliment her.) It's a lot to think about! Add to that anxiety about flirting and making a move, and it's no wonder you've worked yourself into such a tizzy.
So, here are a few basic guidelines (from a woman's perspective) to help manage your anxiety:
1. Compliments are always appropriate
Women put a lot of effort into looking good for dates -- especially first dates -- and it's always kind to acknowledge that. Stay away from complimenting her body on the early dates, which can come off as sleazy. Besides her figure, think about what appeals to you about her appearance.
Does she have beautiful eyes? A warm smile? If you're too blown away -- or, perhaps too shy -- to acknowledge just one attribute, a simple, "You look lovely," or a sweet "You look really pretty," or even "You look great!" will suffice.
Later in the date, after you've gotten to know her a bit, a compliment that isn't based on her appearance would be totally appropriate: "It's really admirable that you took a leave of absence to care for your mother when she was sick. I'm super close with my family, too." Or: "It's so impressive that you've run three marathons! How did you get interested in running?" Or even: "You have a great laugh" are all good.
Following up a compliment with a question or a related piece of information about you shows you're interested and also helps further the conversation -- all good things. Basically, if you like a chick, try to get in at least one compliment during the date, but stop at three. You want to hint at your interest without smothering her with it.
2. For physical contact, every woman is different
In general, light touches are appropriate and not considered creepy. Gently touching the small of her back as you hold the door open for her, maybe holding her hand on the way to and from the car, perhaps a light hand on her knee if you're at a movie or sit-down performance together.
Pay attention to her cues, though. If she flinches or backs away when you touch her, hold off for the time being. Try not to take it as rejection; it doesn't mean she's not interested -- although it certainly could -- but she may just need more time to get to know you before she's comfortable with any sort of physical affection.
Some clues that your date is interested and would likely welcome a kiss at the end of the date: she touches you a lot while you're talking -- on your elbow, your shoulder, your knee, etc.; she plays with her hair a lot, flipping it around, twirling it, etc.; she maintains eye contact with you. Eye contact is crucial; it may be the most important kind of "physical contact" on a first -- or any -- date.
If you have trouble looking women in the eye, you need to work on that. Practice with some of those female friends of yours. Lack of eye contact makes you look insecure, indifferent, or uninterested, and is a big turn-off.
3. To kiss or not to kiss at the end of a date
As for the age-old dilemma, "to kiss or not to kiss," if you're having trouble reading your date's cues or you can't tell whether a kiss would be appropriate or not, it's always best to err on the side of caution on a first date, especially with someone you've met online.
A warm hug and even a cheek kiss are fine. You can always go for a kiss on date two. If a grown woman can't handle a kiss on a second date, the issue is hers, not yours. A kiss on the first date can definitely be sexy, though, especially if it's a really great first kiss that leaves her wanting more (i.e., you don't get too grabby or sloppy).
4. Tell her you want to see her again, and how to handle any rejection
Another important thing to remember: if you're interested in the woman and you think you might like to go out with her again, tell her so. Before the end of the date, say, "I really enjoyed meeting you and had a lot of fun tonight. Do you think you'd like to go out again some time?" If she says "no," or "not really," don't act like an jerk and don't take it too personally.
For all you know, you might not be her type but maybe she has a really fabulous friend she'll introduce you to if you keep it classy. Or, maybe you aren't what she's looking for right now but in a few months you would be.
Regardless, it's never cool to treat a woman like garbage just because your ego's hurt. Plus, it's bad dating karma.
Tell her you had a nice time anyway and thank her for going out with you. And if she says "yes" to a second date, tell her you'll call her in a couple days to set something up and then do just that. Don't wait a week. Strike while the iron's hot. Call within two days, reiterate what a good time you had with her and suggest something fun for your second date.
If she doesn't pick up when you call and doesn't return your message, that means she isn't interested and was too much of a wuss to tell you so on your date. Don't get too hung up on it. Move on 'cause time's a wastin' and there are other fish in the sea.
5. Don't get discouraged; it's numbers game
Finally, try not to get too discouraged if you have "limited success" with dating. Lots of people have limited success. It doesn't necessarily mean anything. It's all a numbers game, anyway.
All you really need is that one person who's right for you, but sometimes you have to go out with dozens of people who aren't right for you before you find that one. If you're having trouble even getting first dates lined up, show your online dating profile to a trusted female friend or two and ask for advice. They might see something that's slipped your notice: blurry photos that don't show you off in the best light, a cheesy headline, a jaded remark about how hard it is to find a good woman.
Be confident! Stay positive. Be yourself.
Keep at it, and follow my basic guidelines for good dating etiquette, and you'll find success eventually.
6. Bonus tip: guy should pay
Men should pay for the first date, so always take that initiative. But, if she absolutely insists to pay for her half and won't take no for an answer, take that as a sign that she's not romantically interested in you and let it go. Some women, myself included, don't want to feel they owe the guy anything -- like a second date -- simply because he bought her dinner.
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