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Dear Roe, I’m 23 and have never had a boyfriend. It’s just never happened for me, and for a few friends too. I’m starting to fret that I’ll never find someone. I go to parties, events, nightclubs the odd time (but I don’t really like them), and try to get myself out and about so I can meet lots of new people. The guys I like don’t like me, or those who like me I don’t like back. I’ve gone on a lot of first dates, but I’ve never even liked someone after the first one and so it’s never gone further than that.

My friends have tried online dating (and I don’t mean Tinder), but they’ve warned me to stay away. I know life plans never work out, but I always hoped to get married at a young enough age that I would be able to enjoy married life for a bit without having to worry about the biological clock ticking away.

At the same time, I always wanted to have a couple of relationships before settling down so I could get to know what I liked and disliked in a partner, while having some fun and learning how to make a relationship work. My parents split when I was four, so I’ve never really seen or been in a working romantic relationship. I’m getting pretty stressed now. What do I do?

Dear Letter Writer,

Darling girl. I feel for you, and mainly because I know my advice is, to some extent, going to fall on deaf ears. If you want a relationship, and if you feel like there’s something missing, and if it’s based on a lifelong desire for a stable romantic relationship, there’s little I can do to change that. But I can tell you something, something that literally anyone any older than you will confirm again and again and again.

Twenty-three is so. Goddamn. Young.

It doesn’t feel like it – it never does. And it never feels like relationships are going to happen for you when they’re not right now. But they will. You’re going to have a relationship you talked yourself into with someone that later makes you think, “What the hell was I thinking?”

You’re going to have a relationship with someone who you constantly feel like you’re chasing, and you’ll later wonder why the hell you bothered running when there were so many people just dying to stand still with you.

You’re going to have a relationship with someone who loves you more than you love them, and you’ll later realise that ending it was the best thing you could have done for both of you. You might have a relationship where you get hurt, badly, and right when you’re wondering if you should bother again at all, you’ll meet someone who makes you realise that all your other relationships happened so you could be ready for this.

But of course you won’t believe this right now, so until the day it happens and you think to yourself, “My god, that gloriously witty, inconceivably wise and irrepressibly charming columnist Roe was right, I should send her an thank-you elaborate gift,”  let’s get practical.

First of all, having your parents split early is hard, and real, and I’ll never undermine that experience or the desire it creates to have a stable family life. But I don’t want you focusing so much on a serious, long-term image of the future that you miss out on glorious, fun and utterly necessary, formative experiences in your present.

I also need you to know that the success of a relationship isn’t solely based on the fact that it lasts forever. Great relationships can end for a myriad of reasons, and they often leave people much wiser, happier and more sure of what they want.

Your parents’ relationship resulted in you – talk about a slam-dunk. But if you think that your parents’ split is still affecting you deeply, giving you anxiety and affecting your ability to be happy now, these ideas may take longer to unravel and sink in.

If you feel like therapy might help you with this, don’t be afraid to look into it. Always work on your relationship with yourself first, before entering one with anyone else.

Secondly: dating. What you need to know immediately is that no one likes feeling like they’re being forced into a ready-made idea of a relationship, and I’m worried you may be giving off this vibe. There’s a difference between being open to a relationship and having a rigid, predetermined mould that you try to hammer someone into.

One thing I’m curious about is your statement that “guys I like don’t like me, or those who like me I don’t like back.” I’m wondering about the kinds of guys you like, if perhaps you’re approaching the wrong audience.

You shouldn’t settle for someone you don’t like, but you should also be aware of what people are looking for. If you’re looking for something serious, but approaching mischievous bad-boy types who are just looking for fun, you’re never going to get what you want.

And what about these boys who like you? Why don’t you like them? Are they too serious, too earnest, do they project an image of a relationship onto you? Could it be possible that you’re doing the same to men you like?

I’m also interested in the limitations you’re placing on yourself. You haven’t tried online dating, not because it doesn’t work for you, but because your friends have warned you off it. My dear, this is silly. If your friends told you that talking to lads in person didn’t work, would you just not try that either?

Online dating offers up a vast world of different experiences of people, and even the people who find something wonderful have to go through a hell of a lot of bad dates and mismatches before they find something. Also, if you’re looking for something very particular, you can say this, and filter your matches accordingly, so you’ll only be matched with lads looking for a relationship.

You also say you’ve never been on a second date. If this is always your choice, this seems extreme.

Again, if you’re instantly repulsed by your dates or if they reveal themselves to be Trump supporters or something, you shouldn’t go out with them for six months – but I’m slightly suspicious about how you’re approaching these dates. Are you giving your dates any leeway?

First dates cause a lot of nerves in a lot of people, and some people are far more relaxed on the second meeting. And are you approaching dates as a fun night out where you can get to know someone? Or are you going in with a mental checklist and appraising your dates for boyfriend material and possible husband material – testing how their twenty-something self will fit into your view of marriage and kids in your thirties and forties?

Neither you, nor your dates, nor anyone else knows at 23 who they’ll be a decade or even five years later – thank fuck. What you want and need is going to evolve, and you’re right to know that a few relationships will help this process. But you have to let these relationships happen, and I’m worried you won’t.

Know that what you think you want is not what actually makes you happy. You might think you want someone outgoing, or someone practical or someone well-read, when actually having someone quiet or goofy or outside-the-box challenges and complements you more, and makes for a more fulfilling match.

You won’t figure this out if you don’t give people a shot, and be willing to see spending time dating as a worthy experience in and of itself, rather than just a means to an end.

Let yourself be willing to be with someone unsuitable, and wrong for you, and just for now. Let yourself enjoy dating, and all the butterflies and disappointments and great stories that it brings. Let yourself be open to the possibilities. Let yourself be surprised. Let yourself be brave. Let yourself be hurt. Let yourself be loved.

Let yourself be young.


I’m a 27-year-old straight woman, and consider myself pretty open-minded when it comes to sex. I’ve been in a relationship for about six months, and my boyfriend wants to have anal sex. Now, I totally want to do this, and have before with other partners – the thing is, every time I’ve done it before, it hurt. My female friends have told me that having a drink or even smoking a joint will help – is this true?

Dear Letter Writer,

Just for any mothers/Gardai reading this, let me give you Dublin Inquirer’s official statement in the event of any legal proceedings:

You’re a bad, bad girl, considering drinking, drugs and sex. Shame on you, get thee to a nunnery, etc etc.

Now, down to business. Having good girl mates to help you with your problems is important. However, it helps if they have the faintest clue as to what they’re talking about, and honey, in this department, your mates are sadly lacking.

Getting drunk or high before anal sex is an AWFUL idea, for one simple reason: being drunk or high doesn’t make anal sex better, it just dulls your ability to feel pain in the moment. And you know what pain is? It’s your body’s way of telling you that something is wrong. You should be listening.

Which leads me to an important question: why are you doing anal sex when it’s always been painful? Sex should be pleasurable for you and your partner, not something that causes you pain and you merely endure because your boyfriend wants to try it.

There’s a difference between being open-minded and not giving yourself permission to say no to things you don’t enjoy. Don’t fall into the trap of saying yes to things just because you think it’s what an “open-minded” person should do.

But if you really want to do anal with your boyfriend, let’s make sure it’s actually pleasurable this time.

One of the many, many reasons you need to be sober and completely enthusiastic about trying anal is that if you’re not relaxed and aroused and aware of your emotions and body, it’s going to hurt. Please note: I didn’t say it “might” hurt – it’s going to hurt.

Unlike your vagina, your anus is not self-lubricating, so any friction or rough treatment can easily result in injury. Ever heard of an anal fissure? It’s a tear in the skin around the anal canal that can reopen and bleed every time you have a bowel movement. Fissures can become chronic and require surgery, which can leave people incontinent.

Real sexy, huh? So yeah, not kidding. You have to take things slow.

Invest in some anal sex toys, specifically designed with flared bases to avoid any awkward trips to the emergency room. Look out for kits with beads, bullets and dildos of varying sizes, and bonus points for kits that allow you to turn each toy into a vibrator.

Give your boyfriend the night off and begin to experiment – first with your fingers (and lube, lube, lots of lube, don’t make me repeat this a million times), then the toys – smallest one first! Experimenting solo is a great way of letting you explore what feels good without pressure or expectation, and get you used to the sensation.

When you’re ready to let the boyfriend back in the bedroom, you’re going to stick with this slow, foreplay-fuelled approach. Your boyfriend is going to spend a lot of time putting his fingers (and LUBE), your toys (LOTS OF LUBE) and, for bonus points, his tongue (SALIVA AND LUBE) inside you.

Some people get squeamish about the last option, but assuming you’re all squeaky clean down there I always err on the side of “if you don’t want to put your tongue inside me, you don’t get to put your penis inside me.” Your call.

Do just this fingers-and-foreplay routine on a few separate occasions just to establish trust and know what feels good.

When you’re absolutely relaxed and turned on, your boyfriend should put some lube on and inside you, and insert two or three fingers. Then position yourself so the tip of his condom-covered penis is against your asshole, making sure the head is covered in – yes, you guessed it, lube. He can then push the head of his penis against you, but not in you.

As he applies pressure, you’ll feel yourself open up a little to take him in. If you’re comfortable, he can VERY GENTLY and VERY SLOWLY push himself inside you. When inside, he’s going to stay very still and you’re going to move, so that you have complete control. When it feels more pleasurable and comfortable, he can very slowly start moving in and out of you, slowly building up speed if it feels good.

This is going to be a slow process, and you’re going to allow it to be so, and not put pressure on yourself to immediately start jackhammering away. But each time he gently and slowly moves in and out of you, you’ll be able to take a bit more in, and after a few minutes of tender maneuvering you’ll be able to move onto stronger thrusting, and before you know it – you’re having full-on anal.

Don’t forget: Condoms are a must, and must be changed if you switch back to vaginal sex, to avoid nasty infections. And make sure to clean your sex toys after use, because, well, eww.

And speaking of toys, you know you’re not the only one who can be penetrated, right? Your boyfriend can receive and enjoy anal sex too – same rules apply, only you’ll need to add a strap-on to your shopping list. A partner who knows what it’s like to receive anal will be much more sensitive and considerate giving it. Just a suggestion.

Do you have a question for Roe? You can submit it anonymously at:

Roe McDermott

Roe McDermott is a journalist, arts critic, Fulbright awardee and sex columnist from Dublin. She lives in San Francisco, where she's completing an MA in Sexuality Studies.

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