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Dossy, 32

dossy.org

Everyone knows that the best place for a web-design meetup is one with free WiFi. But what essential features characterize a perfect first-date spot?

A good date venue has to be a place you'd go to whether or not you're on a date. That way, no matter how the date goes, you're still going to have a good time.

Good web designers have a knack for aesthetics. Given your discerning eye, how should a date dress to impress you?

Appearance, like good design, should be functional and elegant. Dress in a way that highlights your best features. Don't go overboard. Keep your audience in mind. Don't spend so much time and effort that if it goes unnoticed, you'll be upset. Keep things simple, which is actually very hard to do.

Many of the web designers I know are proficient in a number of computer languages. But are they also proficient in the language of love? What's the no-fail pickup line you've used a thousand times?

The best "pick-up" is to learn about the other person and communicate with them in a way that creates a meaningful connection. Of course, communicating with a machine in its language is a lot more precise than dealing with the fuzziness of humankind, which is what makes relationships challenging. A pick-up line that'd probably work on me might be, "Hey, I've been trying to get WordPress to do something. Could you help?" I'm a sucker for folks who have tech challenges to solve. Especially if they're blonde.

I've been with my boyfriend for three years now, and he's never hinted at marriage, or even the possibility of moving in together! Shouldn't he know by now whether I'm the one he wants to spend the rest of his life with? Am I wasting my time?

Most guys don't know what they want to do tomorrow, let alone for the rest of their lives. If you want him to move in and marry you, perhaps you should just ask. If you're going to be passive about it, perhaps you are wasting your time — and his.

I'm twenty-eight and I've never even kissed a guy, let alone gotten dirty beneath the sheets. At this point in my life, any and all intimate acts seem terrifying and out-of-reach, making me unable to relax on first dates. How can I move past this?

Email me your picture, right away. I'll find ways to help you relax. Where would you like to go on our first date?

Matt, 30

www.myspace.com/stingraythebold

Everyone knows that the best place for a web-design meetup is one with free WiFi. But what essential features characterize a perfect first-date spot?

Well, as much as I like the traditional "dinner-and-a-movie" idea, I strongly suggest replacing it with "dinner-and-a-social-activity-that-you-can-both-enjoy." Movies are fun, but even silly things like miniature golf, bowling or just meeting at a coffee shop — WiFi and laptops optional — give you more interaction and a chance to really get a good feel for each other, literally and figuratively. Then, when it comes time for that second or third date, you can get cuddly and popcorn-y with a movie.

Many of the web designers I know are proficient in a number of computer languages. But are they also proficient in the language of love? What's the no-fail pickup line you've used a thousand times?

Humor of any kind is the ultimate potential-date attention-getter. Personally, I equate sarcasm and wit with verbal foreplay. If a girl can dish it out and take it, and match wits with me, then it's on!

Ctrl-Z: the magical keyboard shortcut for "undo" that makes (almost) everything better. Looking back on past bad-date behavior, which conversations and supposedly slick moves do you wish you could undo?

Never ever bring up anything about an ex on a first date. You're potentially starting over with someone new on a date, so this is a huge step backward, and indicates that you have serious baggage. Your date's flight is not going wait for you load it.

I've been with my boyfriend for three years now, and he's never hinted at marriage, or even the possibility of moving in together! Shouldn't he know by now whether I'm the one he wants to spend the rest of his life with? Am I wasting my time?

I personally know couples that have dated for several years, broken up for a year or two, and then gotten back together and gotten married. There is no set time limit for "knowing." If you want to know his thoughts on marriage or moving in, the best thing to do is ask him!



My girlfriend wants to open up our relationship and see other people, yet she insists she still cares about me. Is this the end for us? Should I agree to this arrangement in the hopes that she'll one day realize I'm the only one she needs, or am I setting myself up for further heartbreak?

Sometimes people need to take a break from a relationship to figure out more about what they want. It doesn't necessarily mean the end. Sometimes seeing other people helps you realize that you don't want to see other people. And sometimes seeing other people makes you realize that you weren't actually good for each other. In short, taking a break can give you both a new perspective. Agree to the arrangement only if you can look upon it with that attitude, and have an open mind about it.