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).
11. DON’T be a downer. Going on about your parents’ divorce, how much you hate your job, or the terrible weather is going to put a damper on the evening. It’s tempting to talk about bad news when there’s a lull — fight the urge!
12. If a guy says, “I’m sorry, I don’t usually have much to talk about,” DON’T try to make conversation. Grab your coffee and go.
13. DON’T feel guilty if you’re not interested in date #2. That’s the way the world of dating works. If he proposes another date and the thought of it makes you want to gouge your eyes out, DON’T commit to something you’ll later have to lie your way out of. DO say, “You know, I am really glad we met, but I don’t think we’re a good fit for each other.” If he pushes it, thank him profusely for the compliment of asking you out again, but be firm and get out ASAP.
14. DON’T go on a date with a guy who has sunglasses on in all of his pictures. He’ll ride up all sexy on his motorcycle (with his sunglasses on) and you’ll get all excited. (He even has a perfect beard!). Then you’ll go into a cafe to get a beer and a sandwich and the glasses will come off and his eyes will be tiny and one centimeter apart. Even though you’ll take the sandwich and beer out to the garden out back, and the glasses will go back on, you’ll know about his secret tiny eyes.
15. DON’T go on a match date the first week of February. If it goes well, then he’ll ask you out on a Valentine’s Day date, and that’s too much.
16. If a guy calls you the morning you are supposed to get breakfast and says he’s really sorry but he might be a couple of hours late because his car was broken into the night before, DON’T dismiss it as a lie. It might have happened, and if he doesn’t cancel a date with a stranger to deal with all of that, he’s probably a keeper.
17. DO let him pay and DON’T think this means you owe him anything. He will be expecting to pay; he will not be expecting a hand job because of that.
18. DON’T sleep with him. Probably don’t even kiss him. Hug him, squeeze his hand a little, and if you want to, tell him you’d really rather kiss him but feel like you shouldn’t.
19. DO realize it’s damn near impossible to play games when you’ve met online. You both know you are looking for someone. If you both felt the sparks, it’s pointless to ignore his texts or act coy.
20. And if you’re lucky enough to like each other, DON’T lie about meeting online. It’s nothing to be ashamed of.

Related Posts:

• Online Dating: Be Safe, NOT Paranoid

• Online Dating: Schedule to Meet in Person Sooner, not Later
• Shorter, Fatter, Balder: Men’s misleading online profiles