So, I’m a fairly attractive and well-socialized guy with a self-esteem problem that makes it difficult for me to assert even that I’m fairly attractive and well-socialized. For the most part I keep that under control, but romantic situations are challenging.
Being fairly attractive and well-socialized, I don’t have much trouble meeting women. Many of my friends are women. The problem is getting from being friendly to being physical.
I’m not the Mayor, and this isn’t another friend zone complaint. “Friends” is easy and comfortable, and “more” is — or feels — complicated and scary. I don’t know how to get there, I don’t know how other people get there, and much of the time it seems better to stay put.
What am I supposed to say or do? How do I know when to say or do it? How do I avoid panicking or feeling skeevy?
1) What am I supposed to say or do?
To get started:
- Would you like to go on a date sometime?
- You are really cool and I love hanging out with you. Also, you are pretty. Can we go out sometime?
- Can I buy you dinner sometime?
- There is this cool (thing) happening next weekend. Will you be my date?
- I feel nervous and awkward asking you this, but I would love to take you on a date sometime.
On a date that’s going well (by which I mean you are having fun and think the other person is having fun and you are having a good conversation about stuff you’re interested in and everyone is keeping up and smiling):
- I’m having a really good time with you, thanks for coming.
- You look fantastic. I love that (color on you, thing you’re wearing)
When you feel like you might want to kiss the other person:
- I would really love to kiss you now. Is that okay?
- Can I kiss you?
- Would it be okay if I kissed you?
Leave the magic moment where you know without words to the experts (or Future-You, who has more experience with this). Use your words and ask.
Say the kissing stuff is really good and everyone seems to be enjoying themselves.
- I love kissing you. Could we go somewhere else and do that some more?
2) How do I know when to say or do it?
You don’t. So try saying it when you feel like saying it, preferably as close as possible to when you feel it, when you’re sure the object of your affection is paying attention to you (e.g. You’re already having a conversation that she seems to enjoy – she’s not giving one word answers, looking at her watch, texting/calling her friends, trying to watch a movie.) May I suggest online dating, to give yourself practice asking people out in a context where some romantic interest is the default?
3) How do I avoid panicking or feeling skeezy?
You don’t. You may well panic and/or feel skeezy!
The moment where you go from not-kissing to kissing is fraught with vulnerability and potential awkwardness, and the space between two people who could-be-touching-maybe-but-aren’t-touching-yet can seem infinite and uncrossable. That’s what makes it so awesome and sexy when you actually connect. Nervousness? Wondering if people feel the same way you do? Wondering if you’ll screw it up or they’ll screw it up? These feelings are inherent to sexual and romantic connection and discovery, even for people with a lot of experience. Experience makes you able to be more confident (and handle rejection better over time), but it doesn’t change the vulnerability you feel with a new person you like.
You’ll get rejected at least once. Probably a lot. If you do the asking out sooner rather than later, before you get too invested, and you accept that rejection and/or lack of connection is the default setting, what’s wrong with rejection?
Let’s do some Rejection Math:
I went on about 10 first dates with people I met on an online dating site in the last 6-7 months, give or take.
I turned down AT LEAST 50 people on the spot – either by not replying to their messages at all, or writing back and saying thanks but no thanks. I initiated contact with another 10 or so who didn’t want to go out with me, or we wrote back and forth a bit but never actually made plans. Let’s put the “never even met up” count at 60 for the sake of easy math. I am picky and busy.
Of the 10 I went out with, I liked two enough to go out a second time.
I became great friends with one of them after a brief crush/flirtation period where I clearly liked him more…er, differently… than he liked me (and said so out loud).
I fell in love with the other one and he with me.
That’s 68 nos, 1 maybe-no, and 1 YES!
Rejection is a normal part of dating.
REJECTION IS A NORMAL PART OF DATING.
I was not harming the dudes I didn’t want to go out with by rejecting them, and the dudes who didn’t want to go out with me were not harming me.
If you pre-reject yourself by panicking, overthinking, and avoiding, you will never get to the good parts of life and love.
If you’re looking for some rubric where I tell you signs to look for to help shield yourself from rejection, I don’t have one. Women are people, people are diverse in what they want. All you can do is ask for what you want and be gracious and patient until you get it. If something seems to be going well, watch for reciprocity. People who like you will act like they like you. They will help you out with awkward moments and be proactive about communicating and making plans.
4) What’s the difference between a would-be writer and a published author?
The published author finished a book, sent it out, got rejected, took some feedback, revised the book, sent it out again, and kept doing that until the right person pulled it out of the giant pile of other manuscripts at exactly the right time. It took a combination of persistence, optimism, dumb luck, and the subjective tastes/wishes of the person who read the book and liked it.
P.S. That last thing was a metaphor.
P.P.S. Seriously, that’s all I’ve got. It IS that simple. Every single person who is romantically/sexually involved with another person got there because someone was brave enough to cross that tiny-yet-infinite-space and say the awkward thing out loud.