What’s The Best Dating Advice You’ve Ever Received?

6.09.20

I think most of us are pretty comfortable admitting that we have no idea what we’re doing.

In life, sure, but specifically in love and dating.

And that’s because when it comes to relationships, there really isn’t a “right” or “wrong” way to go about things. All we can ever do is make the best possible decision with the information available to us at the time, and on the odd occasion (read: all the fucking time) we get it wrong, vow to be better tomorrow.

The good thing about making mistakes is that they’re an opportunity for growth – to get ourselves one step closer to figuring out what it takes to make a relationship go the distance. And sometimes, if you’re really lucky, your friends will make the mistakes before you do, saving you some suffering. 

Here’s a selection of the best dating advice offered by readers of The Twenties Club (both male and female), learnt the hard way.


If it acts like a duck, and quacks like a duck, it’s a duck. Don’t waste your time with a duck if that’s not what you want. 

When someone apologises for their actions and then continues with the same behaviour; that’s not an apology, that’s manipulation. 

Never invest in someone based on how much you like them, invest in them based on how much they’re investing in you.

Never pursue a woman solely based on how hot you think she is. Instead, pursue the kind girl, the honest girl, the sweet girl, the funny girl. The sex will be just as good, and the chat will be better in the morning. 

No matter how much you think he likes you – if you’re still single, he doesn’t like you that much. 

As a woman who dates other woman, I’ve set a little rule that works well: Whoever chooses the restaurant, pays for the meal. That way you avoid the awkward conversation of “who’s paying”, and neither party ends up in a situation of worrying that you won’t be able to afford the meal, or put the other person in that position. 

Eat lots of pineapple.

A lot of women are fearful of speaking up about racism or sexism because we’ve been conditioned to believe it means giving up a part of our “desirability”. We cling to our desirability because we’ve internalised the belief that our worth is determined by how desired we are by men. A part of us knows that to speak out, show anger, or be loud, risks us being depicted as “the angry feminist” or “the difficult woman”, something that we know men find highly undesirable, and so a lot of women aren’t willing to call out their boyfriend or male friend. I’m telling you now: give it up. Do not continue shagging your racist boyfriend just because you don’t want him to think you’re difficult. 

Never stay the night at a FWB’s (friends with benefits) house after sex. Sleepovers lead to feelings. Dine and dash.

Don’t fall in love with “potential”.

Regardless of whether you cooked her dinner or she cooked for you, always clear her plate after she’s finished – and don’t let her do the dishes. Also let her serve her food before you serve yours. Guys serve last.

Read Attached by Amir Levine and Rachel S.F. Heller. It completely changed my perspective on why some relationships succeed and others fail.

If you’re insecure about your body, don’t be! Most guys literally can’t believe they’ve got a naked woman in their bed.

Don’t expect someone to know what works for you during sex if you don’t know yourself.

If he’s trying to pressure you into have sex without a condom because “condoms feel shit” – the sex is going to be terrible.

Always remain graceful in tough moments with your partner. You’ll look back on how you behaved and be grateful that you didn’t say something you wish you could retract.

Never complain to your friends about something your partner did before you’ve spoken to your partner about it.

Always pee after sex.

Go for a walk on your first date: A lot of people connect better when they don’t have to make direct eye contact. Plus, if the date goes south at least you’ve got some exercise in!

If you’re unsure if a guy likes you, he doesn’t. 

If you can’t tell people you’re doing it, you shouldn’t be doing it.

If you want sex – make a girl feel sexy!

If his car and his room are a mess, chances are: So is his life. I’m bisexual and can confirm the same rule applies for girls.

Never date out of loneliness. When you date to fill a space in yourself, you are only stifling your own growth.

Always hold the door open for her. Be kind and respectful to staff at restaurants and bars. Let your date walk ahead of you, and never split the bill.

Figure out yourself before making your issues and insecurities someone else’s responsibility.

If you ignore red flags at the start, they will eventually become red stop signs at the edge of a cliff.

An elderly lady once told me that the key to a fruitful marriage is to always sleep naked.

Hold eye contact with her when she’s speaking for Christ’s sake. 

The right person at the wrong time is the wrong person.


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