Dear Successful Date,

Congrats on passing the first rigorous days/weeks/months!

Reaching this point is truly an achievement and if you think dating is tough, you’re not the only one. Trust me, there are so many guys who manage to screw up dating a wonderful woman because of some avoidable boo-boos.

Which is why, after seeing another guy fall flat on his face last night, I’ve decided to share with you men some dating rules of mine that may hopefully help you prevent having the same fate of the unfortunate gentleman last night.

I call them “Raven’s Dating Rules,” — cheezy I know, but this is a fun post, so am just running with it unless you have some better ideas.

Now, just as a disclaimer, you’re already old enough. Use your judgment on whether these tips do make sense or not. Most of them are my own opinions of the subject so don’t treat them as the dating bible, nor slash me to itsy bitsy pieces if you don’t really agree with what I recommend.

They are tips, okay? So loosen up!

And if you have any other Qs or have anything to add on the subject, feel free to let me know by leaving a comment. So anyway, enough with the yak-yak and here goes:

Raven’s Dating Rule 1: Chances of success in taking a woman out significantly increases as you ask long ahead of time…

You didn’t ask me out at the last minute, fully expecting that I’d be free and wrongly assuming that I’m disinterested if I’m not.

Smart boy!

How did you correctly guess that I have so many things in the pipeline that when I said that I’m busy, I’m not playing a game, but really am! You do know am not the type to drop everything in her life (ergo, work, friends, etc.) just for the pleasure of going out with you, right? I don’t even now you so why should I… which is why you are asking me out for us to get to know each other better.

Now, stop comparing me to those immature women you’ve met at Room 18, okay? If I’m not busy, I won’t play games and say that I am. And if I already have plans, believe me, I really do have plans.

Hence, to increase your chances, ask ahead.

You knew that chances of success of me going out with you on a date significantly depends on how far ahead you ask. It’s not rocket science: the earlier you ask, the better, so at the very least, it doesn’t conflict with any event I’ve already planned to do.

For example, if you ask me the day of, there’s an 85% chance that I already have plans (who wouldn’t?). So unless you’re a business contact, wherein which I absolutely have to accommodate the last-minute request, chances are, I won’t break my plans for you. As a warning, don’t go for the business contact ploy: as a rule, I digress from going out with business acquaintances.

They’re kinda messy if you know what I mean.

Anyway, if you ask me the day before, there’s a 70% chance I have plans.

If you ask me three days ahead, chances of actually taking me out increases to around 85%, because hey, at three days prior, if I am still busy at the proposed date, I will in return propose an alternative date when I’m free because you asked in a timely manner,

Now, if you ask me a week or two weeks ahead, I’ll almost always make time for you and meet so long as you’re no weirdo who asked me up his room or felt my butt up the first time we met (e.g., I have no negative impression of you).

At that lead time, I can always move my plans around to accommodate going out with you. If I still offer some excuses despite you asking way ahead AND not offer an alternative time, well then, give up now because I ain’t be going out with you anytime soon.

Raven’s Dating Rule 2: When asking a woman out, be suave, BUT be a man. Just ask her!

Asking me out is really simple:

1) Form a plan on your mind on what you’d like to do on the date.

Gosh, I hate it when I ask men who ask me out what he had his mind, and the best he can utter is, “Uuuuh, you’re the master in restaurants and fun things to do. What do YOU want?”

For me, this just means the guy’s lazy and didn’t do his research, leaving the woman to do all the work in planning the date! Argh.

Sure, my knowing all the best restaurants may be partially true, but still, if I wanted to organize an event, I can do that from work. Pai tuo — can you please come up with a game plan for our date just so I can take a break? Believe me, I would appreciate that thoughtful gesture very much.

Besides, figuring out where you take me is part of the plan. It shows a bit on who you are, which is good, because the reaosn why I’m going out with you is to get to know me better.

Find a place that you like and the food’s delish. A hole in a wall is good too. Trust me, I don’t care how much the dish costs, but for sure, do NOT bring me to McDonald’s or a fast food chain.

That’s just tacky.

2) Gather up the guts, and slip that invite out during a text/phone/mail correspondence.

Do the invite with style — Calling me and asking me out straight out isn’t doing it with style. Sending me an invite to go to your gallery to hang out anytime after 10:00 pm is not a considerate invite. It shows you just want to get laid.

Ask nicely and invite me out at a more godly hour will get you further.

One thing that works is to maybe start an MSN, email or text communication. Do you know the story of the Fox and the Little Prince from the book of the same name? Start slow and if I respond, continue on and start approaching closer and closer on regular periods so I’ll grow to expect it and even look forward to it.

Show that you want to get to know my mind better even though it’s sometimes obvious that you want otherwise. And then extend an invite while suggesting an activity.

Here’s a few good ones: “I like to try out new restaurants. Hey, there’s that suan cai bai rou hotpot place I want to try. You think you’re adventurous enough to give it a go?”

“I do want to watch Sweeny Todd this weekend. Are you free?”

Start talking about Macs, and when girl admits she’s a Windows loyalist, offer to show her what Macbooks are all about.

Guys aren’t the only ones who are dense.

We women are too.

So, the more straightforward an invitation is, the better.

For example, an invitation that goes, “Hey, want to grab dinner Thursday night? There’s a restaurant I’d like to try out near the Heping area.” works a lot better than “Hey, let’s hang out this weekend…” <– vague and shows you’re chicken.

An open-ended question will get you nowhere. For example, I recently received an invite saying, “Let’s meet up soon. Just let me know when you’re free.”

Okkkaaaay.

Guys, listen up, never throw the ball to the girl’s court. Chances are, you’ll be waiting till the US government evacuates out of Iraq before that woman gives you a call. Why? Ha, doesn’t she have anything better to do and be too desperate?

As a rule, we women dislike making the first move in inviting you out. I know you hate us playing games, but look at it from our point of view.

1) There are tons of people we can call — so why call you? I can hang out with friends I’m already comfortable with. Why call a random stranger? If he’s interested, he will call.

2) We don’t want to build up guy’s bad habit of laziness. If we take the initiative now, chances are, we’ll be left taking the first move going forward! Again, if he’s interested enough, he will call.

Someone said that guys are like fishermen and women are like fish who choose to be caught. It’s kinda true. There has never been a happy ending with me taking the first move with a guy. It always ends up badly because the guy takes you for granted.

Maybe it’s because you never know if the reason they’re going out with you is because you’re available, or if they really, really like you.

Chances are, it’s the former because hey, if he’s interested, trust me, he’ll be in touch. You have your mutual friends, he can google you, but trust me, he will find you.

So to conclude, if you ask nicely and smoothly way ahead of time, am sure, if the girl’s even slightly interested, you’ll snag that date!

Raven’s Dating Rule 3: Dinner preferred for first dates. How to make a date memorable? Talk! Get to know each other!

The worst dates I’ve ever had if there’s such a thing is at a movie theater. There you are, munching on fattening, calorie-filled popcorn and huge sodas, wasting 2-3 hours of your date, just staring up the screen.

It’s even worse if the movie sucks too. I remember my date and I watched “Ice Age 2,” which was absolutely terrible.

Movie dates are great for the third or fourth date, but avoid them for your first two.

What does Raven recommend for first dates?

Admittedly, I’m a bit biased towards dinner.

You see, the best first dates I’ve ever been to were in a quiet quaint restaurant, and you’re just relaxed and talking about nothing and everything. It was enjoyable enough that we then moved to take walks at the Daan park, or continue on with desserts at Swensens till wee hours of the morning.

If you can’t really talk to your date, abandon ship. It’s not going to work out that much anyway…

The reason why dinner dates work better is because it introduces a romantic aspect to the hopefully blooming relationship. It’s hard to get in the mood if it’s in the daytime. What’s more, if you’re lucky and the girl’s reciprocating the interest, it’s easier to prolong the date if ever.

Take advantage of prolonging the date by offering some variety. Always have Plan B or an idea on what to do after you have dinner so you can change the scenery, making the woman think that you are at the very least, interesting.

Suggested Plan Bs: Having dessert at Dong Qu Fen Yen/Swensens, a walk at the park (e.g., SYS Hall, etc.), grabbing a drink at a nearby lounge bar (if you’re in Anhe area) or going to an amusement center (really good suggestion in my book!).

Save the lunch, teas, coffee, lounge bars invites for the 2nd dates. Start with dinner first, and if everything is in plan, proceed with the rest.

And here’s another tip, better to offer red/white wine than Japanese sake. I’ve had Japanese sake on dates, but they’re just awkward because they never really get you tipsy enough to loosen up.

Oh, and never order food that are inconvenient to eat — Sure, I know you’d like to eat a burger, buffalo wings or that eeky black-colored octopus pasta. But it’s not really sexy if sauce is everywhere, or your teeth are black.

That goes for men and women alike.

Raven’s Dating Tip 4: Don’t ever fall at the “Friends Zone!”

People unconsciously fall on the friend’s zone. That’s a sucky place to be in especially if you’re interested. You don’t really kiss friends… that’s just disgusting.

How NOT to fall in the friend’s zone? I can’t really say, but I can share some clues on when I put guys on my friend’s list. They are as follows:

1) You don’t pay for the first date.

Look, I’m no gold-digger and don’t mind paying for dinner, but if you let me pay for the first one, sorry, but you’re a friend. If you’re romantically interested, you’d want to set a good impression and pay for the first dinner.

I remember one time I went out with someone who asked me out. We had a nice dinner at Brass Monkey and the bill turned out to be NT$800+. He looked at the receipt, and out of courtesy, I offered to pay around NT$300, which he took!

Jeez, for NT$800, I could very well treat him to dinner. But if it’s a first date, for goodness sakes, take out that wallet and pay! For one, it offers me the opportunity to treat you back the next time around (and I have treated guys in return), and for another, it’ll pay back in the end.

I’m a firm believer of guys paying for the first dinner, and maybe I can pay for the movie tickets or the taxi.

I absolutely hate splitting the bill right then and there. And if you’re too exact with the split, it won’t be long till I split. And to hell if I ever go out with you again on a 1×1 basis!

Likewise, if I insist paying for dinner, that’s not a good sign. It shows I don’t want to be obligated in going out with you again ’cause I don’t owe you any favors.

2) You yak about your ex-girlfriend.

As much as possible, do NOT mention the ex.

It tells us that you’re still not over her, and you have emotional baggage we have to contend with if we continue to go out with you. We already have baggage; we don’t need yours to make it heavier.

There are a million topics to talk about. Choose one of them. And if we ask about her, downplay her presence.

A good answer is that you broke up because you’re incompatible, and leave it at that. Bow out gracefully against bashing your ex because it introduces negative thoughts in the conversation. If I hear a guy complain that his girlfriend cheated on him repeatedly, I’d think he has bad taste in women because he loves to accept abuse. If a guy states that his girlfriend dumped him because her parents disapproved, I’d leave thinking about what my parents would say about this guy.

Your date is not your shrink.

Don’t make her one.

3) You don’t have any passions except to play video games.

Don’t be a bore — Talk about things you’re passionate about.

There’s nothing sexier as seeing the twinkle in your eyes as you revel on that trip you took to Cambodia, the thrill you get after finalizing a deal at work or you painting.

We don’t really need to share interests. For example, you can go bicycling all you want, or you can go hiking. But at the very least, so long as you’re interested in something, that makes you interesting.

I’ve seen dates where both people are not even talking. I can imagine that both of them need to get the hell out of there, but cannot be too impolite about it.

The purpose of the date is to get to know each other, and what better way to do so than to ask questions and share interests?

4) You treat me as a sister.

It’s one thing to respect that woman and keep your distance. But do it too much and we think you’re disinterested.

The best move I’ve ever seen was with this Hong Kong guy last year.

After dinner, he moved right beside me in the sofa and continued talking to me. In a way, he invaded my personal space and introduced the prospect that he’s not just taking me out just to be friends. Sometimes, his hand would brush by mine and he would lead me through the door as he opened it.

Trust me, I did not place him in the friend’s zone at all!

Of course, there are limitations.

A few weeks ago, there was a guy I met at the party who kept on touching me incessantly. Maybe he was tipsy but since I met him only at that party, I didn’t really care about him taking the liberty to hold my waist, hug me close or giving me a kiss on the cheek.

Unless you’re French, you do not kiss me repeatedly! And even if you are, you should at least control yourself…

Truth be told, I have stayed away from this lecher because all I kept thinking is that this guy just can’t control his hands or himself. I would be stupid if I went out with him because who knows what he’ll do…

So lesson is, do invade my personal space but don’t go overboard. Do the push-pull strategy of moving one step forward, and two steps back. It shows you’re not desperate, and that’s quite attractive.

Raven’s Dating Rule 5: End the date sweetly. Make her want you more…

So anyway, the date is nearing an end and you’re wondering if you’re getting a kiss goodnight in the end…

Sadly, you’re in Taiwan so women here are a bit more conservative than in the US. You may make an attempt but if you fall flat in your face with the girl declining your overtures, say bye-bye to Date #2.

Take things nice and slow. If you can, take her to her door (unlikely because of the convenience of the MRT), but it shows you’re considerate and gentlemanly.

Whether you’re at the door or at the MRT, if you can, manage your raging hormones and DON’T ASK HER TO GO HOME WITH YOU! Say goodbye nicely, maybe give her a warm hug and tell her you had a great time. If you’re brave, give her a friendly peck on the cheek and a friendly squeeze hug.

Don’t say you’re going to call if you’re not.

We women hate that.

Just say bye and leave it at that. And if you say you’ll call, call the day you promised. Otherwise, we’d think you’re playing games and dump your sorry ass.

Oh if you do drop her at the MRT, for goodness sakes, give her a message/call in an hour to make sure that she’s home safe. At the very least, that shows thoughtfulness.

Leave the sexual overtures after she’s more comfortable with you. Play only a winning hand or risk never seeing her again. If she sleeps with you early, both of you know it’s nothing serious. And we both know that if she does, you’ll think she’s a slut.

So leave her waiting for more.

Again, don’t screw up such a lovely date by asking her to go home with you. Let her look back on the evening with a smile, and trust me, you’ll be talked about and positively analyzed by her and her girlfriends in the few days afterwards.

Anyway, getting late. Thanks a lot for your patient reading and hope it helps somehow!

Night night!