Rule #52- Getting Off The Sidelines (and Going on a Date)

Via National Maritime Museum, Magnus Manske

Just like when knowing someone is worthwhile and a good match for you, and you can just feel that tingly feeling in your bloodstream when they walk into the room, it’s also important to make the distinction who NOT to date. Or more importantly WHEN not to date.

On the one hand, there is a lot of pressure if you are single to date. Because maybe, just maybe, the next blind date you go on will turn out to be the one. Now, I’m not saying that they won’t; just that sometimes you might feel pressured into going out on dates you don’t really want to be on, with people you don’t really want to be with. Worse yet, you might convince yourself, for any number of reasons, to give people a chance – just one more date, and one more – when they aren’t really right for you.

The problem is finding a balance between not dating at all, and not getting “out of shape”.

Well, dating isn’t exactly a muscle, but it does  require exercise and growth. If you never go out on dates, or form relationships while waiting around for Mr. or Miss Right (that person who will be the right fit for YOU), how will you know what to do – hell, or what to look for when they come along? The fairy tales that nourished our mind’s as children perpetuated this myth that when the right person magically appears, everything will just fall into place. But what we tend to ignore is that fighting the dragon was a hell of a hard job.

The only way to build a relationship is with a lot of hard work. The only way to know if the relationship isn’t working for you,  or if this person isn’t working for you, or if the dynamic  between the two of you is just not right, is experience! And unfortunately for us, experience demands quite a bit of sweat, tears and heartache!

While some lessons are best learned the hard way (you hopefully won’t repeat mistakes that burned you the first time around after you refused to heed the sage advice of others), This may be of help:

1. Don’t date unless you feel like putting the effort into this person. Because if you don’t feel like investing your time in them to “see where it can go”, there really isn’t any point in starting something up. Mostly because this isn’t fair to them. That doesn’t mean you shouldn’t give people a chance, but if you do decide to give things a go, then do it properly.

Sometimes. it’s also important to recognize potential. If you meet someone special, or have a click with someone new, give it a chance and see where it goes. It might not work out, but you will have learned something new. Every interaction, be it good or bad, teaches us something, provided we are able to look deeply into ourselves and the relationship and reflect on it. And I promise you this (cliche warning) – when that someone does come along, you will be glad that you learned all those lessons beforehand.

2. Don’t go on a date with someone you intend to dump at the end of the evening!  Whatever your motive is, pity, pressure from your mum or even the prospect of a free dinner, just don’t.

3. Go on dates with people you feel you already have things to talk about, or in common. If you already have a good starting point, be it attraction or things in common, there is probably a greater chance it isn’t going to be a complete waste of an evening.

4. The less you get out, the more you are not going to want to go out. Because let’s face it, the thought of staying in your warm bed with a hot water bottle, and all the episodes of the shows you haven’t  caught up on, is way  more tempting than having to make small talk with a stranger. But you have to break this cycle! It’s time to stop dating your laptop (even though it may very well be better company than your prospective date) and go out!

5. Maybe it’s time to un-friend zone that really cute guy/girl that you have been constantly flirting with for months (or just admit they were never really in the friend zone to begin with)! You already know you have tons to talk about and that you will both have a good time. You probably shouldn’t come to this decision lightly (not to mention out of desperation), but it’s probably worth considering.

6. Learn to open up more to people. Not dating for ages will probably make you suspicious of new people, and make it harder to open up to them, connect on a deeper level and form a relationship. My advice is to make some new friends as an exercise, or open up more to your old ones; it’s important you learn how to trust again, even if you were hurt in the past. You need to learn to be vulnerable with people, because let’s be honest, it’s vulnerability that is the basis of a good relationship.

7. Go out with friends more! No I don’t mean necessarily to pubs and dancing, but rather to social events. House parties, concerts, singles mixers in the religious denomination of your choice. There is a much higher chance that you will run into new people with whom you have more in common if you already share a social circle, community or some interests, like God or your favorite band.

8. Reclaim your mojo!  Chances are that if you haven’t been on a date in a while you probably don’t feel all that secure about the whole thing, so do something to reconnect with yourself. Try salsa dancing or yoga or buy that new dress or those new shoes you’ve been salivating over, imagining how jaw-droppingly good you would look in them. Getting in touch with your body, or just plain pampering yourself, will make you feel much more confident in you – and by extension, with that special someone.

9. Sometimes it really isn’t a good time to start a new relationship (stress from work/family issue and so forth). It’s perfectly fin to put your foot down and tell your pestering  aunts (yes, even the ones that only exist in your head), that now is not the time to start something new, because you just don’t have the emotional and mental capacity for it. That said, “I’m focusing on myself/my career at the moment” is sometimes not just an excuse we give to someone we’re trying to blow off, but a line we may be constantly repeating to ourselves in order to avoid putting ourselves out there.

You just have to accept that part of dating is risking getting hurt, but that isn’t an excuse not to try! 

Rule #41- The ‘I’m Not Sure If This Is A Date’ Date


via Joxemai

Let me set the scene for you (because we’ve all been in it, at the very least once or twice in our adult lives).

You’ve arranged to ‘hang out’ with someone; It’s most likely evening, there is alcohol on the table, and the sexual tension is buzzing around almost tangibly (at least you think it is… isn’t it?!). You really like them, but because of the nature of the encounter, you’re not sure if the feeling is mutual.

I think this has only happened to me twice, and both times it was confusing and rather agitating. Especially, when it comes to working out if someone is into us ‘that way’ or not.

So what can you do about it?

1. Most of these errors happen because we aren’t sure if the other person is interested in us (sometimes I wish humans could read each other’s minds, and then I remember what a god awful idea that would be). Therefore, we need to investigate things a little further.

Not that I’m against treading lightly. Call me old-fashioned, but I believe that’s what a FIRST DATE is for. When you define the activity as a date, the boundaries are clear, you both know where things stand. You’ve both agreed to get a drink and see if there is ‘something there’. 

Just don’t let yourself end up in ambiguous situations! If someone says “let’s hang out next Friday!”,  Just go out on a limb and ask “like on a date?!” .

Things might not work out romantically, but at least you are both on the same page. 

2. Fear not, if you do find yourself in this unfortunate situation, there are a few ways to get out of it.

For starters, you can always be blunt and ask them (the worst that can happen is that you will end up realizing it was an awkward misunderstanding, that you can either laugh off, or end the evening prematurely with the most uncomfortable hug ever). Or you can go for plan B (this is what I usually do): show you are interested! I’ve fondly named plan B. flirt your bum off.”

3. They may not be into you at all. People flirt for so many different reasons; to make themselves feel good, they genuinely think they are just being nice (and really didn’t mean to flirt at all), they want something from you (not necessarily sexually); the possibilities are endless! 

My rule is, if I’m not sure, I either reciprocate to show I’m interested and, see where it goes – or let it go and move on.

4. If you aren’t interested in the other person, and you think you may be on a date, make it CLEAR that it isn’t a date. You don’t have to phrase it that way, you can tactfully slip it into the conversation, but make sure that they know you’re not interested. 

(Try and do this ahead of time on the phone. Make it clear up front that it’s a hang out as ‘just friends’, and try not to wind up in the most ‘couply’ spot in town).

The best relationships often grow out of friendships. Just don’t allow yourself to get stuck in the ‘does he/she like me?’ limbo! Because it’s frustrating as all hell.

Rule #38- Exclusivity

via Hanh Dung – Son, Bùi Linh Ngân

A few years ago I took a short trip to New York (City). In-between Broadway and cocktails, my host, a friend from back home, admitted how difficult she found dating in the city.

She was used to dating one person at a time, and having exclusivity a given from the get-go. This new concept, of dating a few people simultaneously, was a foreign concept to her.

Which made me wonder, what guarantees us exclusivity?! Going out a couple of times, dating for a month, maybe even three,  having sex on a regular basis, only once, ‘I love you’s’?! (and let’s not forget those wonderful people who just completely neglect to notify their significant others that they don’t believe in monogamy). At what point is it SAFE TO ASSUME you’re the only one? At what point is the OTHER PERSON the only one?

What do you do when there is such a fine line between cheating and ‘still seeing other people’?! 

I have to say that I spend copious amounts of time pondering this rather daunting  question, and I’ve reached the conclusion that there is no social convention as to when one should adopt monogamous relationship patterns. 

Isn’t it wonderful, how there is just no social consensus on this sticky matter? (where are ironclad dating laws when you need them?!)

So how does one deal with this rather awkward situation? 

1. I feel like if you’ve gone out with someone more than a couple of times (let’s say three for us indecisive types), you do it because you are interested in them. You aren’t necessarily picking out a band for your wedding just yet, but you are interested in pursuing something. 

If you do see a future, STOP hedging your bets! Sometimes it’s a good idea to risk everything for a higher return. The more you are willing to invest in the person you just started dating, the more you will stand to gain from the relationship. Taking a risk is a good thing, and with relationships, you have to take a chance on someone else if you want things to go somewhere. 

2. TALK TO THE PERSON YOU ARE DATING! If you feel there is something there, ask them if the relationship is exclusive, or tell them you want it to be. Never assume anything these days! (because everyone has a different idea on the subject). Some people, because that is what is acceptable in their circles, won’t stop seeing or even sleeping with other people unless you define the relationship as exclusive. 

3. Ask yourself if you would be comfortable if the other person found out you were still seeing/sleeping with other people… If the answer is yes, you wouldn’t want them to find out, then you are de facto hiding it from them. In which case…

Make a decision! Either stop messing around, or break it off with the person you are seeing, because it isn’t fair to anyone involved! 

Rule #35- Sexual Premises

via Lies Thru a Lens, Lost in Thought

I’m really going to try hard and keep a balanced point of view throughout what I am about to discuss; but I am a woman, and therefore a little bias.

I used to think about sex in a very liberal open minded sort of way. Otherwise known as “who cares if you finish as long as you had fun and intimately connected with your significant other”.

I feel like most women (or at least many women) see sex this way. It’s more of a bonding exercise (no pun intended), and not necessarily meant for their own satisfaction. 

Meaning, that sex is fun, finishing during sex is even more fun, but it isn’t a ‘must’ every time. 

And we accept this.

Why is this a BAD premise when approaching sex?

1. Unless you are trying to get pregnant, you are probably having sex for your own/mutual pleasure. Sex has a point, it’s called an orgasm! (It’s that fun toe-curling part at the end, or halfway through, and then again if you’re lucky).

Now, you may not feel like you’ve been selling yourself short when you don’t have one, but you are! Orgasms are wonderful things! 

And allowing yourself to miss out on a surge of chemicals that do wonders for your well being is you, missing out! 

2. Every time you have one of these you tend to want more of them (you know the drill).

When you don’t orgasm you are less likely to want to have heaps of sex (because it’s less gratifying). You may even get bitter and resentful about this over time (and possibly even a little bored with the proceedings). 

(obviously not a good thing for the relationship). 

3. You might not necessarily think that not always finishing even bothers you.

In my opinion, this is the worst harm. It wouldn’t even occur to you to have sex and for your partner not to finish. Yet, we find hundreds of ways to reinitialize to ourselves why when we get the short end of the stick, it’s alright. 

Now, thank god, attitudes towards sex are forever evolving; both culturally, and with age. I don’t think that on the whole woman don’t feel it’s their right to derive pleasure from sex. But we do have quite a bit of a way yet to go when it comes to our day-to-day sexual routine and bedroom expectations.

So who’s at fault, and what do we do about it?

Blaming generations of male indoctrination really isn’t the answer here. At the end of the day it comes down to our inability to communicate our needs to our sexual partners. I don’t think for a second that the person you are sleeping with doesn’t want you to crack the window with enthusiasm.

The problem starts with our demands in the bedroom, and not being able to make them known (physically or verbally). TELL THEM WHAT YOU WANT/ENJOY/NEED/LIKE! (And if you don’t know what it is you want, it’s about time you start figuring it out). 

Tell them that you finishing isn’t optional , its part of the exercise! 

 I hope my pseudo rant wasn’t too one-sided, but come on ladies, sex is just as important in a relationship as long talks, staring into each other’s eyes, and romantic getaways. 

(And besides, it is also a great deal of fun).

Rule #31- That Awkward Moment When You Run Into Someone You Used To Date

via Intense Moments on the Streets of Vienna, russavia

A couple of weeks ago I was strolling along, minding my own business and fumbling around for something in my bag. I look up, and  lock eyes with this guy I went out with a couple of years ago (if you haven’t read the post about this particularly awful date, do so now). Not having enough time to duck behind a rubbish bin or a parked car, I was forced into a very awkward, very smiley conversation with him.

There is no strict protocol about what to do or how to behave when you run into someone you once went out with. The harder the break-up, the harder the accidental run-in (here’s to hoping you aren’t stalking them and haven’t orchestrated the whole thing).

I personally become over-smiley and laugh way too much; but to be fair, this is how I choose to deal with most awkward situations.

You’ve pictured this very moment in your head (about a million times); you’re always wearing a sexy red dress (and are possibly sporting an awesome new pair of boots/hot guy). You smile casually, say hello (noting happily that he’s put on weight and his new girlfriend is in no way prettier than you).

But in reality, you are probably going to run into him at that precise moment that you’re late for work, just got into a huge fight with your mother, and haven’t washed your hair in three days.

Rules For Bumping Into An Ex:

1. Things you should NOT, under any circumstances, do:

A. Veer of course and “casually” dive behind a dumpster; your’e not fooling anyone! Don’t hide or ignore them; you are better than that!

B. NEVER ask: “so… are you seeing anyone?”

First of all, you don’t really want to know if he is. Secondly, it’s the worst kind of small talk imaginable. Also, and most importantly, he may misunderstand and think you are interested!  Which can either lead to him turning you down, or even more awkward, him calling you. 

C. Don’t flirt! 

DDon’t talk about the amazing new guy you’re dating! It’s disrespectful and not very nice (yes, I know he was the one who dumped you! But he’s now fifty kilos heavier, and unemployed to boot. So no need to rub it in).

E. Don’t be mean or spiteful.

F. You had a nice chat, you smiled just the right amount, you are almost out of the danger zone. And then, as if out of nowhere, you blurt: “We should really get together sometime”.  You don’t want to hang out, you don’t really ever want to see him again; it just seemed like the polite way to say goodbye.


2. Keep the conversation short, simple and friendly.

Just say hello, be polite, inquire about his health, and then you can get the hell out of there.

If you really can’t face him, for whatever reason,  just smile when you walk past (acknowledge him) and keep on walking.

Rule #28- Cracking ‘The Code’


In Jane Austen’s novels we have alluring glances from across the room and suggestive smiles. These days we have coded texts and muddling emails. Modern dating lingo is chock full of innuendo, vagueness, and  ways of saying things that mean other things. In short, things have gotten pretty damn confusing. 

In theory, to avoid awkward conversations, it’s great to have these codes. ‘Awake?’ instead of ‘Fancy a shag? ‘It’s not YOU it’s ME’, instead of: ‘It’s not me, it’s YOU’. And so on…

The only problem is, that no one has ever printed out a manual and handed it out on street corners. How awesome would that be?! 

If we ALL had the same phrasebook, we could be as illusive as we liked, with no consequence. But alas, there is no such magical pamphlet in circulation.

 I absolutely despise not knowing where things stand. I think we ALL do. 

There is nothing more annoying than being messed around with.

So, let’s wade through this mucky subject together and try to make sense of things.

Rules for Cracking The Code:

1.  There are certain things that EVERYONE takes to mean sex.  If, and only IF, you can be certain that the other person is going to understand, use a euphemism. Otherwise, avoid confusing each other; it really is counterproductive.

2. If you feel uncomfortable using certain words, or saying things that are either downright or borderline dirty; sit down the two of you and decide on your own code (that you both understand).

(Yes, I do realize that this can be kind of silly. But, it can also be fun and bonding, so give it a go).

3. Codes are fun, games are fun; but at some point they will just wind up causing trouble. Instead of spending hours playing guessing games with yourself (and your girlfriends), just ask him what he meant. Boy, do I know how hard that is (for months I thought ‘LOL’ meant lots of love. Needless to say, that lead to a few exceedingly uncomfortable moments, and ‘LOL’ isn’t even cryptic).

Most cryptic language we use is for: asking someone out, dumping, sex, or any other slightly uncomfortable topic. It helps minimizing rejection on the one hand, but on the other it’s a pain in the tush. So please, please, think twice about the words you use, and don’t be afraid to tell other people to be more clear with you! Coyness is only beneficial to a point.

Rule #27- The Flirting Loop

via Haras national suisse HNS

It’s past midnight, and you have been texting for over and hour. You are at work and laughing hysterically at an email you just received, even though it wasn’t really that funny (much to your co-workers’ chagrin). You’ve braved dinner,  ‘just as friends’, but really just wanted to skip dessert and rip each other’s clothes off.

If all of this sounds familiar to you, you, too are a victim of the Flirting Loop!

The Flirting Loop; that dreaded situation you end up in where  you both like each other, but can’t quite get past the flirting stage. I’m not going to lie to you, it’s not easy to get out of, but it is possible (with a little determination and some charm).

You may have already tried every flirting trick in the book, to no avail, and it may be a case of shyness. Either way, it is time to brake that vicious circle!  

Rules for Moving Forward:

1. You will never be able to bring the whole situation to closure unless you can make up your mind about whether you like this person or not. I think that a lot of these ‘hot and cold’ games are a direct result of the fact that you are just not sure if you like each other ‘that way’. 

Sending (and feeling) mixed signals is what landed you in this mess in the first place. So, the first step out of it is deciding what you want.

2. Flirt responsibly! Flirting has a purpose , it’s a tool to let someone know you like them (and to get free shots when you’re sitting at the bar, but let’s leave that aside). If you flirt with everyone all the time you will confuse the people you are actually trying to impress. 

3. The easiest way out, is to just directly ask the other person if they are interested. But because we are not all that blunt/brave/not afraid of rejection, the chances we will just put ourselves out there like that are slim.

So, instead, we are left with the more tricky option of being conniving about the whole thing. This option is not fail proof, and leads to a lot of misunderstandings and frustration. Therefore, one of you should just take a shot of liquid courage and make the first move.

By make the first move, I don’t necessarily mean you have to lean in and kiss the other person (and by NO means ask them if you can kiss them; huge mood killer).  Just make it very obvious that you are available and interested IN THEM!

This is the tricky part… But I have come up with some creative solutions:

# Find a way to spend more time alone together (so you can get to know each other. Maybe this will help you finally realise if you are interested or not).

# Don’t send mixed signals! I said this before, and I don’t know how much I can stress how important this point is.

# Find a mutual friend who knows if he is dating anyone and snoop around a little (just to make sure he is single).

(You don’t need to go into full on stalker mode, just do a little recon).

And you know what, ladies? If all else fails, just turn up the charm. Tap into your irresistibly funny/sexy/confident side! But every once in a while we should take matters into our own hands and confront the situation. After all, aren’t five minutes of rejection better than four months of endless pining?