Sometimes guys ask me for my advice. Stop laughing at the back.

Although I’m as incompetent as the next person, feeling my way through sex and relationships like a horny blindfolded girl groping for the light switch, people occasionally email me and ask for help with their problems. The following predicament concerns a guy who wants to make his fantasy come true, and it struck me that there’s a theme which runs through most emails I get about this subject: whether it’s throatfucking, swinging, threesomes, or something beautifully sweet and simple like the one below, quite a few ‘how do I achieve my sexual fantasy?’ emails share a common theme. So, to try and kill a few extra birds with my stone of shoddy advice, I asked the guy for his permission to post the question, and my response.

Please chip in your own advice in the comments – I’m not an expert, and I am frequently wrong about things.

The problem: how do I make my sexual fantasy come true?

I am obsessed with girls and especially the female body. I absolutely love the female body and how it reacts to sexual stimulation.

I am 19, male and I haven’t had actual sex yet. I have been masturbating and fantasizing for several years now and really want to finally have some sexual action with a hot/cute girl. I don’t want full sex with her but I really really want to make out and pleasure her. I am very curious about how it feels for a girl and how close sexual stimulation feels with her body and words.

So as you can tell I am absolutely mullered by the fantasy of making out with and pleasuring a hot/cute girl who’s OK with not having actual sex.

The thing is: I live in a Christian community and I’m not really attractive or athletic and I don’t have a girl friend. I’m extremely introverted and so I think it’ll be while I’m in my mid or later 20s when I ‘d find a girl friend.

And my parents would wonder what I’d be doing (and against it) if I just went into town to hook up with a girl for a bit. I can’t be openly driving to people’s houses or strip clubs or whatever with my parent’s car.

So I think the best bet would be that I take a walk and have the girl pick me up while I’m doing that and us make out in the car or something like that.

But so far I haven’t found a legitimate website that I can find actual local girls to hook up with for free. I live [location redacted – somewhere rural in the US]. Do you know of any legit and free sites that will allow me to possibly find a girl willing to do this with me?

So far all I have found are scam sites and ones that I need to dumb paid membership for. And for me, I really can’t afford that risk atm. I’ve tried CraigsList but that’s all a bunch of scams..

Oh what am I to do?!?

Answer:

The good news (OK, the fantastic news) here is that what you want isn’t in any way unusual. There are lots of people who want to make out – they want the awesome touching, horny kissing, etc, but not necessarily the sex. Perhaps because they’re not ready for sex, or just because they don’t enjoy sex as much as the other parts. But I assure you, there are many people who want this. So you’re in a good position.

However, there’s a really big problem with your exact situation, and that is that you seem to want a very specific thing, and you don’t seem willing to do anything even vaguely out of your comfort zone in order to achieve it: you can’t drive anywhere, you won’t pay money, you won’t use free sites because of scams, you won’t speak to women because you’re shy. In short: your easily achievable fantasy becomes almost impossible because you need it to land directly in your lap with very little compromise or effort on your part.

If I knew what the effortless solution to your problem was, I would have bottled it, sold it, and be typing this on a gold plated laptop right now.

I don’t blame you at all – this is not my way of calling you a wanker. It seems that you are worried about so many things that all seem insurmountable. Instead of trying to overcome one, or all of these issues, you have made them conditions of your fantasy and I think that’s why you’re struggling to achieve what you want.

To sum it up, your ideal fantasy is one in which you kiss, touch, and generally have sexy fun with a girl without having penetrative sex. Big tick in that box: loads of people like doing it, so your pool of potential partners is huge. But you don’t want to have to speak to a woman much, or develop a relationship with her, because you’re shy (totally understandable, by the way: some of the guys I’ve been hottest for have been shy). You don’t want to pay for membership of a dating site (and who does? They’re pricey!). You can’t use a free site because you might end up getting scammed. You don’t want to have to drive and pick her up in case your parents find out (again, understandable, if you think that the consequences of that would be horrible for you). Basically you want all of your ideal conditions met. And that makes giving you advice almost impossible, because any advice I give would mean compromising on one of your conditions.

So, bearing that in mind, here are three advice options:

• Keep trying with free sites (I am a big fan of OKCupid, and I think you have that in the States, but if anyone else has suggestions please leave them in the comments!), and trying to weed out possible scammers wherever possible. Accept, though, that you will meet people on it who are either scamming you, who want something slightly different, who might want a relationship before makeouts, or who don’t have their own car: that’s just how humans work, and it’s impossible to recommend a site which can deliver you someone guaranteed to fill every aspect of your fantasy.
• Go pro. When I read the first half of your email it occurred to me that if you really want this specific thing, but without having to develop a relationship, then speaking to a sex worker could be ideal. Find someone in your area (on Twitter I see adultwork mentioned often by sex workers, so I’d recommend heading there first, unless any sex workers have better suggestions that they can leave in the comments, pretty please!) who you can have this experience with. This involves compromising on your ‘free’ rule, but it’s one of the simplest ways to guarantee that you can have what you’re looking for.
• If you don’t like the above ideas, then the only thing I can recommend is to compromise on the ‘shy’. Which I know I know I know is hard to do. Speak to women, and try to develop a relationship with one who would like to do this with you. You don’t necessarily have to be boyfriend and girlfriend if that’s tricky for you, it might just be a girl you get along well with who also wants to have a go at making out and touching: it’s fine. I know this is scary if you’re shy: incredibly so. But it won’t get any easier if you never do it, and if you don’t manage to find a girl who’s willing to do this with you, you may still have met some nice people and had fun with them.

And that’s it, I’m afraid: I don’t have any magic bullets. As I said originally, I’ve been asked similar questions quite a few times, and I struggle to give advice because often I think what the guy wants is for his fantasy to just happen. You’re luckier than others in that usually their fantasies are things that are a bit more niche or kinky, so their original pool of potential partners is limited by the fact that only a small slice of the population would be up for the act itself. But either way I’ve seen lots of variations of “I need X but I have to get it without doing A, B or C”. As with you, they’re all usually legitimate concerns, and understandable problems. The trouble is, when you add them all up, the only way the fantasy is actually going to happen is if a passing woman just happens to fancy making out with the stranger she’s driving past, and has the confidence to shout out of her car window and ask for it.

So, to summarise, my advice would be that you need to pick one of your conditions and either compromise on it or make some effort to overcome it, or you need to cross your fingers and hope really hard that the very unlikely happens, and do a hell of a lot of wanking in the meantime.

Oh, and worry about the car situation when you get to it.

Once upon a time I was sitting in a tiny greasy bar with a boy, when a rose seller came along. She had a basket full of dozens of roses, each one tied up nicely and ready to be hawked to the nearest soppy romantic.

I growled my customary ‘don’t disturb me in the pub’ growl. The boy looked interested.

Romantic acts

Romantic acts don’t have to be the obvious ones: diamond rings, flowers, breakfast in bed and the like. But these things do have a certain kind of charm, and if you want to impress someone, it might be easier to reach for a bunch of flowers than a deeply personal something-or-other that has the potential to backfire.

I have a deep and sincere admiration for people who perform romantic acts. Those who know exactly when to shower love, and in exactly what quantities, to make someone melt.

But it’s not easy. One person’s romantic gesture is another’s worst nightmare, and the success of the gesture in question all comes down to how well it’s received. I was reminded of this recently when a friend told me a story about a guy she knew: madly in love with one of his friends, he journeyed the two hours it took him by train to turn up at her house. Rather than knocking on the door and sobbing his undying love directly at her, he decided to be a bit more subtle. He knew she was a chess lover, so he left two chess pieces: a king and a queen, on her doorstep, along with a dozen red roses and a letter that explained how he felt.

“Aww,” said I “how romantic.”

“Fuck that,” said she “it’s creepy as all hell.”

The roses and the romance

I hate that this is the case, but it is, and I have no idea why. Romance is a fantastic thing, and I’m sure many of us would love to have more of it in our lives. But it seems like the main thing that makes a difference between a romantic act and an inappropriate one is something the romancer can’t always know: whether your crush actually fancies you.

If they do, you’re a hero. If they don’t, you’re a loser. And possibly a creepy one at that.

I’m going to tell you two different versions of the roses story now.

Version one:

The rose seller approaches me and the boy, and my heart is beating far too quickly, hoping against hope that this shy, nerdy first date doesn’t turn into a mush-riddled disaster. All I know about this guy is his name, his occupation, and a story he’s told me about how his sister once pushed him off a swing. I don’t know him well enough to anticipate whether he’s cheesy enough to think the ‘rose for a pound on a first date’ gambit is a good idea.

He does.

Red-faced, I accept the rose. Later that evening we part, and his post-date text seems unnecessarily gushing. We never see each other again.

Version 2:

The boy grins at the rose seller, and I whisper to him “seriously, dickhead, don’t buy me a rose. I’d only have to carry it home.” He squeezes my leg under the table, looking slyly at me in the way he knows makes me want to lick him. For the last two, three, four years I’ve alternately mocked and raged at him for his lack of romance, his lack of spontaneity.

“How much for a rose?” he asks the lady with the basket. I’m looking away now, too embarrassed to make eye contact and show that, secretly, I actually really want a bloody rose, even if it’s drooping slightly and will end up getting left on the bus. She tells him how much they cost, and there’s a long silence. Ages. Aeons. Millennia pass while I stare at the rings of liquid on the bar and fiddle with the plastic twizzly gin and tonic stick and just wish he’d get on and tell her ‘no’ so that we don’t have to eke out the embarrassment.

Years, or perhaps five seconds, later, he speaks.

“I’ll take the lot.”

And he hands over note after note after note from a wallet that’s rarely opened unless it needs to be. And I walk home arm in arm with my boyfriend of many years, drowning in roses and love.

There’s no right way to do romance

Arguing with my friend over the chess incident made me sad for the boy who’d tried so hard. For his unrequited love and his inability to read the girl’s reaction. Assuming they were both in earnest, no one did anything wrong here: it’s just a misjudged gesture and a mutual tragedy. But from my friend’s point of view, it’s a stupid guy making a desperate play for a girl who’ll never want him.

As she put so succinctly: the difference between creepy and romantic often just comes down to whether they actually fancy you.

I don’t think I want this to be true.

I’m an online dating evangelist – I think meeting people on the internet and then going for drinks with them (in a safe public place, etc) is one of the best ways to meet likeminded and potentially shaggable people.

As an evangelist, however, there’s a conversation I’ve ended up having a few times that makes me incredibly uncomfortable. It goes something like this:

“Remember you told me to go on OKCupid?”
“Yeah. How’s it going?”
“Well, I’ve had a couple of quite good dates. But I’ve also been sent some hilarious and awful messages. And oh God this one person had a profile so bad it was hysterical. I’ll send you a link…”

Please don’t show me the money

I don’t want to see your links. I don’t want to see the people you think are so funny that it’s worth going to the trouble of finding their profile again, copying the link and then emailing it to me. I’m human, of course, and so naturally I find the flaws, foibles and fuck-ups of other humans inherently funny. There’s nothing I like more than hearing how unrelentingly shit other people can be, because it makes me feel like less of a blundering oaf.

Tell me about it, by all means. If you’ve spotted a dating profile where someone’s used a UKIP quote in the ‘things I like’ section, then that’s well worth a pub-time anecdote. But I don’t want your links.

There’s something so deeply personal about an online dating profile that even the idea of other people seeing mine (I’ve wiped it now, so don’t go looking) makes me shiver with cold dread. Like showing your CV to a work colleague who has known you for years – someone who knows that most of what you’ve written is – at best – rose tinted and – at worst – bordering on fantasy.

Mistakes, misogyny and mockery

I don’t like it when people lie on internet dating profiles. When they send messages that are presumptuous or rude. I don’t like it when they make sexist statements or offer arrogant critiques of people’s profile photos. There are many things that I not only don’t like, but that will have me wishing slapstick comeuppance on anyone who comes across as vaguely right wing.

But I don’t want you to show it to me. There are two reasons for this:

1. I have probably seen it, or something like it, already. No, really. I’ve done a lot of internet dating, so if you send me someone’s profile picture along with an amused email about how he’s odd because he included a photo of his dick, the best reaction you’re going to get from me is ‘so?’ I’ve seen quite a few dicks – attached to profiles, emails, and (if I’m really lucky) actual men. I’ve also seen messages where people just say ‘how r u sexy’, or write clumsy erotica, or offer to be your slave forever. Unless it’s a spectacularly unusual message or picture, my reaction is likely to disappoint you. If you want someone to be shocked by it, you’re better off sending it to your mum.

2. I’m uncomfortable laughing directly at people. Sure, if a friend trips on the way to the bar and accidentally spills a beer over someone I didn’t like much, I might have a bit of a snigger. But there’s a world of difference between the odd giggle at someone’s flaws and an anonymous shredding of someone who has laid themselves bare for you in the hope that you’ll approve. The shredding is fine, but when you’re shredding someone and I have to look into their eyes – even if they’re separated by a net connection and the knowledge that they’ll never hear what I have to say about them – there’s a feeling of discomfort that just isn’t enjoyable. If you asked me to kick a kitten I wouldn’t feel comfortable doing it just because you assured me it was dead and wouldn’t feel a thing. It’s still not a fun thing to do.

I’m not saying people on dating sites are all amazing and wonderful, nor even that in mocking them you’re a horrible person. What I am saying is that if you want me to join you in appraising and critiquing, I don’t need to see who they are.

Knowing me, knowing you

This brings me on to my final point – and it’s a very important one. Be wary of being too judgmental about people when you’re telling someone else about them. Recently a friend of mine (a new member of OKCupid, on my wholehearted and overenthusiastic recommendation) sent me a profile of a guy she thought she liked, and told me that he’d ruined things by having ‘massive sex issues.’ Meaning to incite a good old giggle and a session of bitching, she invited me to offer judgment about his ‘freakish’ foibles.

Unfortunately for her, his ‘freakish’ foibles sounded pretty hot to me. Moreover, based on a slightly blurry picture and his style of profile writing, I had a sneaking suspicion that I’d already sampled them.

She didn’t reply to his message.