The Difference Between Being Sexy and Being Creepy

When I was new to dating, I would read conflicting advice on the internet like the following:

  • “Yes means Yes. A gentleman will always ask for permission before trying to kiss me.”
  • v.s.: “You weak person. Be a man! Don’t ever ask for a kiss because it’s creepy and will kill the mood.”
  • “Nice Guys are creepy because they are infatuated but hide their true intentions.”
  • v.s. “Players are creepy because they hit on everyone.”
  • “If you like someone, you should ask them out on a date.”
  • v.s.: “People should see me as a person with a unique personality and a career, not a sex object.”

So the problem is that if I fail to ask someone out on a date, I’m creepy. But if I do I ask them out, I also run the risk of being creepy. If I ask for a kiss, I’m creepy but if I just go for it, I might also be creepy.

It got so confusing that I actually saw a counselor about this and he had a very simple piece of advice:

You are creepy unless your love interest also wants you.

SNL actually makes fun of this in a skit called “Sexual Harassment and You“, which gives the advice that to avoid being creepy, you should “Be attractive” and “Don’t be unattractive”.

My take on it is this: In American culture, men are expected to make the first move. As a result, you always run the risk of not just being rejected but also being unfairly accused of being creepy. Life isn’t fair but you have to take risks to get a date or romantic relationship. Here are some additional tips:

  1. Talk to someone before asking them out: Ask questions, show interest, and get to know her at least a little. The healthiest relationships involve compatible personalities, not good looks. So if you are looking for a long-term relationship, you should at least find out if you have any amount of compatibility at all. If she can’t even hold a short conversation with you, she isn’t interested or compatible.
  2. Increase physical intimacy one step at a time: Most people will expect to be kissed within 1-3 dates or they will think that you are either creepy or not interested. You should increase the level of intimacy over time e.g. from least to most: hug, hold their hand, sit close to them & stare into their eyes, kiss.
  3. For sex, you absolutely need to ask for permission: Both people need to be sober, of legal age (the definition varies from state to state), and capable of giving consent. It is rape otherwise.
  4. Look for signs of wanting more or less of you: Consistently open body language, touching you back, laughing at your jokes, and inviting you into their apartment are all positive signs. Closed body language, letting go of your hand, and one-word answers to your questions are all negative signs. It’s all about getting good at social calibration and feeling whether the other person wants you. If they keep giving you negative signs, you should respect their boundaries, back off, and look for someone else who actually likes you. This one time, on a third date, a girl invited me into their apartment, got me to sit next to them, started touching my arm, and stared into my eyes. I got nervous, failed to read the signs, and didn’t kiss her. She assumed that I didn’t like her.
  5. Build social skills and confidence: through doing activities. Dating is one of the most complicated social dances. You need a solid foundation in order to build rapport with your love interest.
  6. Get more attractive through self-improvement: whether that’s getting fitter, more educated, more wealthy, employed, better-groomed, or better-dressed. The dating market is an economic market. As cold as it sounds, people date each other of similar value. If you want someone more attractive, you have to be more attractive.
  7. Don’t be so obsessed with looks: I know we all want the hottest person but are you dating someone for their personality & long-term compatibility (and they just happen to have good looks), or are you dating a mannequin? People who are physically attractive get hit on all the time so they are more likely to reject you.

If you are unhappy with the people you are attracting, make yourself a better catch first. Look yourself in the mirror and ask: “Would I date me?” If not, work on self-improvement. It’s true that people who won the genetic lottery and naturally have good looks don’t have to work anywhere near as hard as you, but that’s just life.

Lastly, I was amused (and saddened) by a Reddit user’s surprisingly accurate definition of what is creepy:

She calls him creepy … Because he’s breaking social conventions/norms. Attractive people are supposed to flirt with attractive people. Unattractive people are supposed to flirt with unattractive people.

The conclusion is that you have to take risks and you always run the risk of rejection – sometimes brutal rejection. You can reduce your chance of rejection by making yourself more attractive through self-improvement.

Until next time my friends, keep dating!


The Secret to Getting a Date

During my years of singlehood, I heard many theories about how to get a date. I can now confidently say that I’ve filtered out the bogus theories, leaving you with a set of solid principles for developing healthy, long-term relationships. By definition, healthy and long-term means that there are no “pick-up artist” techniques listed here.

  1. Always do activities: that you either enjoy (e.g. tennis) or that improve yourself (e.g. going to the gym or taking a night course in public speaking). Try new activities occasionally. Also, don’t do knitting, Zumba, or anything else dominated by women unless you actually like the activity – otherwise you will be viewed as creepy.
  2. You will then meet acquaintances: This will also give you a chance to practice social skills, which are crucial for dating. Note that it is important to get to know people regardless of their age, gender, religion, etc. because of point 4.
  3. Some of these acquaintances will become friends: These will probably be people who are similar to you (e.g. age, personality, interests, …).
  4. Your social network will keep expanding: By spending time with people, you will meet more people. Interestingly, you will actually meet more new people through acquaintances, than through friends, because acquaintances can connect you to people from radically different social networks.
  5. Through luck: you will eventually meet someone that you click with and probably likes you back. Ask them out on a date.

There are three important points to emphasize:

  • You have to keep doing activities: so that you keep improving yourself (social skills, confidence, expertise, etc.) and keep meeting new people. Meeting someone special happens eventually (which can be a long time!). Don’t just go to one or a couple of activities and then give up. If you make a permanent habit of doing activities, you are doing the only thing you can do: increasing your chances and hopefully having some fun in the process.
  • Women are looking too: There is someone special out there who is trying to find someone with your exact personality. She may be struggling to find you. So use that as motivation to find her! When she realizes how much you click, she will make it obvious that she’s interested, because she wants you and you’ve been hard to find. In contrast, someone who doesn’t make it obvious probably doesn’t like you.
  • You should supplement this with online dating: Note that online dating is less likely to work out compared to the above five steps because it involves strangers that you know next to nothing about. However, you can get first dates much faster so it’s still a valuable tool – at the very least for dating practice.

One final bit of information that is important but frequently omitted: If you are physically attractive, you can pretty much ignore all of the above advice and still get a date very quickly. My friend Jacklyn is beautiful (and intelligent, for that matter) and she gets asked out just by standing at the bus stop or sitting in a coffee shop. For her, “be yourself” is great advice.

But if you are unattractive like me, dating can be exponentially harder. You could be single for years like I was. But you know what? I still met someone by following the above advice. Life isn’t fair. All you can do is work on increasing your chances. I kept doing activities when I was single and I eventually met my true love due to an unexpected introduction by an acquaintance. That’s what people mean by “when you stop looking, you start finding”.

Until next time my friends, keep dating!