How do I hit on someone respectfully? Your questions answered

Question: As a guy, how do I express sexual interest/make a sexual advance towards a woman in a clear, direct, but respectful/respectable way?

Answer:

Without a doubt, this is the MOST common question I’m asked by hetero guys.

It’s hard hooking up these days, because society gives us so many conflicting messages about how we’re supposed to conduct ourselves. We’re stuck between old attitudes and new; traditional views on masculinity, and modern advice about being ethical and respectful. The old-school attitude is that men should ALWAYS make the first move, because that’s the manly thing to do. Then there’s the post-#metoo philosophy: women just want to be left alone, and creeping on someone is a total asshole move.

I understand why some guys might feel trapped between these two positions; frustrated, confused, or nervous about doing the wrong thing. Truth is, there’s no single correct way to do this stuff. Everyone is different – and what individual women want differs too.

I suspect that many women do want to date (and hook up). We simply need to feel safe and respected. What we need from you to feel this way will vary, depending on the person. But here are my basic ideas for approaching the women you’re attracted to, and trying to ensure they have a good experience.

Note: This isn’t me telling guys what they SHOULD be doing. This is the stuff I do myself when I approach anyone. I think it works equally well for all genders…but if you’re a dude that’s anxious about accidentally invading a woman’s personal space, it could be extra handy.

Don’t try to control the process.

However this turns out, I’m proud of myself for being brave enough to ask.

Picking up isn’t a theatre performance that you can direct. It’s more like a dance, with one person taking the first small step and the other person taking the next. We grow trust and connection through conversation, flirting, and body language. With each step, either party has the chance to move closer, or retreat.

You can’t control whether your advances result in a hook up. You only have the power to take that small step. If circumstances are right, you’ll both make an effort to get things happening. If it’s not working out, that process will slow to a stop. And that’s the way it should be – we’re not all designed to fit well together. There’s nothing wrong with this; it’s just part of the dating experience. It’s essential to pay attention to the signals, so you know to back away when it isn’t happening.

Concentrate on making the best approach you can (or second step, if someone else has already hit on you!) Forget about trying to control the outcome. It’s out of your hands.

Think about her needs, not just yours.

I wonder what she wants right now? What’s going to make her happy?

I have this theory about creepiness. I don’t think it’s about being a bad person – rather, I think we become creepy when we’re only thinking about what we want from someone and forget to see them as a human being. It’s certainly happened to me a lot when I’m out on the town – as soon as I meet someone, they start looking me up and down and I know they have no interest in my personality because they’re too busy wondering whether I’ll fuck them.

And here’s a confession – I’ve been creepy too. I’ve invaded the personal space of guys, harassing them even when they weren’t interested. Because I was so focused on what I wanted (sex, duh) I wasn’t paying attention to their feedback. I made a lot of people uncomfortable..and of course, I didn’t get laid. Nowadays, whenever I find myself becoming obsessed with someone new, I stop and ask myself, ‘What do they want right now? What might they want from me?’ This helps me slow down and take an interest in them as a person, rather than treating them like some sort of sideshow prize I want to bag.

Thinking about the other person and observing them means you’re less likely to miss the signs that tell you to back off. If you see your object of affection looking nervous or uncomfortable, it becomes easier to withdraw tactfully (rather than just continuing on like an oblivious, socially-awkward steamroller). Sometimes when I take a good look at the situation, I realise that they don’t want to be interrupted by me at all, and my observation saves me from being obnoxious.

Be honest about what you actually want.

“I think you’re awesome…would you be interested in having a drink some time?”

If ‘creepy’ means only thinking about what you want, here’s something that’s doubly creepy: focusing only on what you want, then trying to hide your agenda from the person you’re chatting to.

In my old clubbing days, you could see this on the dance floor all the time. I’d be doing my own thing to a bit of nineties grunge, and a guy would sidle up and hover nearby, without saying hello. I could tell he was there for a reason, but he couldn’t quite bring himself to ask for a dance (or for my number). Yeah, it was creepy. And awkward.

It would be much easier if they’d just asked. Then I could have said,’yes’ or ‘no’ and we could all have gotten on with it.

We often hold back from asking for what we actually want, because we’re afraid of being turned down. So we hint and wait and hope…and all the while, our potential date is picking up on these ulterior motives. A hidden agenda can seem sinister, even if your intentions are good. I find it’s best to be direct about what you’re actually looking for.

For example:

“You seem interesting, want to talk?”

“It was great meeting you. I feel like we get along really well – want to hang out some time?”

“Hey, thanks for dinner. I think you’re amazing and I’d love to take you home, would you be into that?”

The direct approach takes sensitivity. It’s not a matter of walking up to a stranger and saying, ‘Wanna fuck’? Remember, start the dance slow – make an offer that’s appropriate to the situation. Then the other person can choose to accept or reject it. This is information you need – it’s much better to find out now than to waste everyone’s time. And being able to ask – showing that you’re not afraid of rejection – makes you appear more confident, which is an attractive characteristic.

Invite a ‘no.’

“Tonight has been fun. I’d love to take you home, if you’re down for that? It’s totally fine to say no, by the way.”

This is a REALLY EFFECTIVE strategy, and it’s something not many people practice. When we ask for something as personal as a phone number, a date, or a kiss, we’re putting our potential hook-up partner in a tricky situation. This is especially true for women, because we’re often raised to feel that saying ‘no’ is rude. Worse, many of us have experienced guys who took rejection badly and got angry. So we might be feeling pressured to agree to your suggestion, even if you haven’t actually pressured us yourself.

Note: guys often feel pressured to say yes to sex too, for a variety of other awful reasons. So, as I said above, this approach is useful for all genders.

Feeling uncomfortable and nervous really kills the mood. Helping us feel safe is essential, if you hope to get laid. The way I do this is by inviting a ‘no’ whenever I ask for something:

“Hi! You seem really awesome, can we talk? A ‘no’ is totally welcome, just so you know.”

“I’d love to make out with you right now, but please feel free to say no if you’re not down for that.”

If it’s a particularly tricky situation (such as someone I’ve just met or who looks nervous) I’ll also give them an ‘easy out’ by making an offer and then walking away to allow them time to consider it. This works well for hitting on guys in bars – I pass them my phone number then leave, so they don’t feel pressured to explain themselves if they’re not interested.

“Hey, you seem great and I’d love to buy you a drink. I’ll be right over there if you decide you’re interested.”

“I reckon we get along really well – here’s my number. No need to say anything now, just give me a call if you’d like to hang out.”

Inviting a ‘no’ means that if your crush says ‘yes,’ you’ll know they mean it. There’s nothing better than knowing someone is one-hundred-percent into you.

Accept that you might fuck up – and learn from it.

What could I have done better? How could I do it differently next time?

One of the hardest things about sex and dating is that we often assume we’re supposed to get it right first go. We’re supposed to magically know exactly what to say or do, and if we screw up we feel ashamed. I’ve definitely done things in the past that made other people feel uncomfortable, and when I realised what had happened I felt like a terrible person.

But a bad person isn’t someone who makes mistakes; a bad person is someone who refuses to learn to do better.

We’re all capable of noticing what went wrong, and trying to improve the next time around. Often, it’s just a matter of paying more attention, to ensure you don’t get caught up in your feelings and forget to consider the other person too. Or if there’s a particular bit of the process where you often get stuck (asking someone out, for example), it might be worth talking it over with friends (or a therapist) to see if they have any ideas on how you could improve.

This stuff takes practice. If you feel awkward and imperfect, you’re perfectly normal.

Here are some useful questions:

Could I have been clearer about what I wanted?

Did they seem uncomfortable? How could I help avoid that next time?

Were they giving any signals I should have picked upon earlier?

Could I have acted more confidently and honestly? How?

What DID I do right? (Don’t forget to give yourself kudos for doing your best!)

There you have it – my personal method for making a sexual advance, while still treating my crushes with respect. Like I said, this isn’t a ‘you should’ type of conversation. I just hope that by sharing my way of doing things, I might give you a few ideas that will help you connect with the people you’re interested in.

Originally Posted on The Art of the Hookup

Photo by Michael Discenza on Unsplash