10 Ways to Ace Your First Online Date

So, it happened. He winked. You IMed. After enough flirty conversations over the phone, you both realized it was time to see if the chemistry held up in person.

That. Is. Scary.

Your first real date with an online mate can be so intimidating. Will he look like his picture? Will you look like your picture? Will you have things to talk about? Will you find him as funny over coffee as you do over G-chat?

It’s not easy to ace a first date, but here are some tips:

1. DO let him take the lead and make plans. If he’s not trying to impress you and show initiative on the first date, when is he going to?
2. DON’T be afraid to speak up when it comes to planning. If you’re a vegetarian or hate sports, don’t let yourself end up in a situation that might make you both feel awkward.
3. DO casually let your date know what you'll be wearing. "I'm at the table by the window in a blue dress!" It makes it less nerve-wracking when you're walking in to the date.
4. DO try something interesting and active! Beer or coffee are fine, and that's probably what you'll do, but how about getting breakfast at a Buddhist temple? Going to a flea market? Or taking the bus two cities over for a tour? DO be open and DON’T freak out if it doesn’t go perfectly. Getting lost together can be more fun than you’d expect.
5. Even if hiking is one of your favorite things to do and is in your profile and his profile, DON’T go hiking on a first online date. It seems like common sense, but it's often proposed.
6. DO wear something classy and keep makeup simple. Aim to impress, not intimidate. Jeans and heels and simple dresses with appropriate hemlines (he can see your amazing legs on the next date) are always safe bets. And guys like simple makeup, so save the smoky eyes and red lips for another time. It should compliment you, not be a distraction.
7. DON’T dress unsuitably for the activity. If he doesn’t give you many details, it’s OK to ask! If he says, “I know a great place to grab a drink,” press on and say, “Great! Am I OK to wear my heels straight from work or are we playing darts?” Err on the side of ease; you can still be sexy in flats at a nice sushi place, but it’s hard to be comfortable when tottering on too-high heels at a burger joint.
8. DO avoid bringing up topics you’ve already covered in your initial chats.
9. DON’T have a list of rehearsed questions (“What was your best…? What is your favorite…? What is your dream…?”). Still, if your date briefly mentions something they’ve done, responding with, “Oh? Did you like it?” and then, “Why?” can lead to really good conversation.
10. DO hold your liquor. Sure, a glass of wine is going to take the edge off your nerves, but getting sloppy can lead you to overshare. Pace yourself, no matter how anxious you feel. Make it a rule to always reject an offer for a third drink, any shots, and smoking pot (which will happen).

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