Dating dilemmas solved


We get that we’re meant to be all about the love rn, but honestly, sometimes we wanna tell Cupid to go stick his arrow… somewhere else. Whether you’re negotiating those tricky first steps, or considering deleting Tinder/Bumble/every app ever, adopting 11 dogs, and declaring yourself a Dating-Free Zone, here are some dating dilemmas to remind you that you are not alone.


I’m just a girl, standing in front of a guy, waiting for him to ask me the hell out. We met through friends like two weeks ago, I know he’s single too, we’ve been messaging a lot, and there’s been C.H.E.M.I.S.T.R.Y. from the start. Should I make the first move?

It sounds like you’re pretty sure something should be happening between you two, but one of you just has to push the situation out of neutral and into drive. Girls are always being told (subtly or otherwise) that we’re meant to wait around for the guys to work up the energy, and the nerve, to ask us out, but that’s just crap.

From your POV, you should be the agent of your own love life, which means taking action when things aren’t going down the path you want. And for him, asking people out is scary, whatever gender/sexuality you are, so give the guy a break and do the asking yourself! Do you really want a guy who’s intimidated by a woman who knows what she wants? If you do, by all means wait. But if you step up and swing, all he can say is no, in which case, it’s not meant to be anyway.

Good luck!


I’m a 6 and the guy I like is definitely at least an 8. Do I have a chance?

Whoa, time out, this is not the NFL/NBA/insert-other-sports-league-here draft. Stop playing the numbers game – which is subjective anyway. Either this person is into you or they are not. Get to know them without seeing that 8 floating above their head, like a cartoon.

And if you need the numbers analogy, find you someone who knows you’re an 11 but loves you even when you’re acting like a generous 2.


I’m soooo sick of the standard first date drinks. It’s so repetitive, and it never really helps me get to know someone anyway. Any suggestions for a first date activity that’s less yawn-worthy?

OMG so many! Good first date ideas:

  1. Take a class in something you’re both completely new at. Laughing over collapsed pots/smudged paintings/a quickly unraveling sushi roll is a solid bonding experience you can’t replicate at a bar.
  2. Mini golf. The funnest way to gauge their competitive side, plus you have a chance to talk/banter while you walk around.
  3. A theme park, but only if you have the same thrill-seeking levels. Standing in those lines is a true test of how compatible your conversation and patience skills are.
  4. Go on a walking tour. You can choose from historical ones, ghostly ones, artistic ones, ones all about food… There’s an option for all, so wrap up (preferably in an AKIRA coat, but you do you) and get ready to learn.
  5. Have your palms read. Even if you think its bogus, it’s something to laugh over (depending on their verdict on your love life…)

Top tip: Do not go ice skating, if you or they haven’t been since that kid’s birthday party in 7th grade, unless you want to spend the second half of your night in the ER getting X-rays for a possible fracture you may or may not have got while standing still on the ice.


Urgh, I’m single on Valentine’s Day AGAIN. Normally I’m totally happy living my independent life, but all the coupley stuff everywhere I look is making me feel left out. If I have to stand next to another couple making out on a train at an inappropriate proximity to me, I will scream. How am I meant to stay sane?

Man, it sucks that this holiday is getting you down, especially when it sounds like you’re usually content with your single status.


It’s hard to believe when it feels like you’re the last single person left in the world, but most people have totally been there. Seriously, even the ones who seem like they’ve been couples forever, and especially the ones who are all loved up about someone new, and all the people in between. At some point, they probably felt like they would never be on the other side of that single/coupled-up equation. And one day, they might be back with you, and you might crossover.

Until then, remember that Valentine’s Day is always gonna be the worst day to be single (except any time your mom is suggesting you contact ‘that nice Mike from first grade, I hear he’s a lawyer now’). Once all the rose petals have died, and the cards are in the trash, and the only chocolates left are the gross mint ones no one wants, it will calm down and you can remember how great it is that you get to watch any TV you want, eat whatever and whenever you want, and never have to find someone else’s dirty towel on the floor.

And one day, when you actually want it, it will be you grossing out other people in public places.


I’ve only been dating the girl I’m with for a couple of weeks, and although I really like her, I don’t know if it’s ‘let’s spend Valentine’s Day together’ serious yet. How do I find out without making it weird? And what do I get her? Help!

OK, this is both tricky and obvious.

Firstly, do you want to spend Valentine’s Day with her? If you do (it sounds like you do) find a specific activity you think would be fun (hint: see those date ideas above. Not ice skating. NOT ICE SKATING.) Then message her, like you normally would, and make it casual. Don’t be self-deprecating, like: ‘I don’t know how you feel about us and where we’re at or if you have other plans, but I was thinking maybe we could possibly do something together on Valentine’s Day.’ Be direct and flirty. ‘Hey, do you wanna play mini golf on Valentine’s Day? Whoever loses buys ice cream after.’

If she says she’s busy, play it cool, and reply, ‘No worries, we can do another day instead.’ If she says flat out no, well hey, you guys probably weren’t going down the same tracks, and it’s her loss.


If she says yes, and you want to get a her gift, keep it super casual but still personal. Get a funny card, and maybe her favorite chocolate or a book you think she’d like, or even just go all-out cliche and get her flowers. But since you’ve only been dating for a short time, she probably won’t expect you to get her anything. Just bring your sweet self, and see what happens.

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  • Natasha Lavender

    Thanks! To each their own 😉

  • Julie Brackley

    Very entertaining and funny (except there’s nothing wrong with mint chocolates)



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