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The other day I got thinking about an old flame. This was from back in the day when I had no clue how to seduce a woman. I thought the right way of doing it was to go all Rome and Juliet romantic on her, to the point where I was very close to serenading below her window.

(thankfully for everyone involved - especially her neighbours - I didn't go that far). I wrote her love poems, as I did to all the girls I fell for back them; I supplicated to the extreme; I called her and begged (yes, I did get her phone number, early on before she realized what a little pussy I still was).

(Quick sidebar: Nothing wrong with writing love poems, but for the love of all that is good don't drown a girl that you've not already seduced with them, and make sure it's not all saccharine-sweet stuff that you could find on cheap valentines cards. Hold back, and don't feel a need to show her all of them.)

Escalating at the right tempo

At one point I wore her down. We met up. I managed to show myself from a good enough side to get invited along to a night out with her friends. I played the mysterious stranger well enough out of pure shyness to get her to come see a movie with me.

I escalated quick enough to overcome some of the hesitation my early shower of poems had induced - I kissed her; I caressed her in ways that made her tell me it felt as if I was making love to her then and there, outside the cinema.

(One of my big strengths has perversely been that while I was struggling with massive approach anxiety and was totally clueless about how to initiate conversations with women, once I got past that, I was and is totally shameless about escalating - arguably this was originally because I didn't understand normal social boundaries well enough to get embarrassed about moving quickly at that stage)

We walked towards her train, and before we parted, we made out again, and she could feel my erection, and she clearly liked it, and she liked that I wasn't the slightest bit shy about it.

I had passed the test.

I had escalated consistently as long as I didn't meet any significant rejection. I took it further than she was used to, but with a confidence that swayed her to let me. It was passionate. I didn't flinch or get shy when she signalled she knew she turned me on.

Escalating too slowly

We talked on the phone the following day, and I went to hers. We chatted, kissed, watched some TV, while making out more.

This repeated several days.

After several days, while making out, she put my hands on her breasts, and I massaged them a bit, while otherwise acting a bit like a dead fish.

I failed that test.

After she went home to her parents for christmas, she called me to tell me she didn't want to see me any more.

She told me straight up that I hadn't moved fast enough. She'd had to signal she wanted sex with me, and even then I failed to act. I had proven I wasn't "mature enough".

Her mom agreed.

Yes, she had discussed my lack of initiative to move beyond groping her breasts with her mother. Women does that kind of stuff. But if a woman does that kind of stuff, you failed a long time before that.

Reality is it has nothing to do with being mature in most senses, and everything with acting like a man. Intellectually and in every other way, I was a man, but emotionally I was insecure and full of anxieties and boundaries I did not know how to get past.

I don't think I've ever been too slow to escalate again since then in similar situations, but I still find new situations where a woman is ready for me to escalate further and I only realize after the fact.

The irony? It wasn't actually because I was all that worried about escalating that I didn't that time, but because I a few months earlier had one of only a couple of cases where I had sex without a condom with a girl I couldn't be guaranteed was "clean".

I went to get checked because I was sure I'd end up having sex with my flame, and was told the initial tests were inconclusive and given antibiotics as a precaution. The final tests came back clear - it'd just been some irritation. But by then it was too late... Last time I took risks like that.

However the effect was the same: Escalate too slowly, regardless of reason, and you're out. And arguably by the time I got tested, I'd already waited too long - the extra delay just drove the point home quicker.

You rarely get a second chance.

I did. Twice. I managed to beg, grovel and wear her down again. In both cases she questioned my masculinity flat out, and clearly pitied me more than were attracted by me. It was clear she liked my personality, but the way I acted meant she couldn't possibly see me as boyfriend material.

In one instance she held my hands and looked at me and told me my hands looked feminine because of my nails (real issue: I was too lazy about grooming to cut them often enough). I couldn't believe my ears, and tried defending it (bzzzt. wrong; failed test again), when the real issue was not my nails at all, but the fact that my behaviour meant I came across as feminine, and so she was testing me, and finding ways to validate her conclusion when she didn't know how to validate it logically.

Her emotional response was that I was not man enough, so she rationalized it in every way she could.

But her gut response was right: I was not ready. Had I not failed there, I'd have been a simpering little syncophant in any relationship with her, and driven her away in disgust later, or we'd both end up stuck in an unhappy situation. As much as it hurt at the time, in retrospect it was a lucky escape.

Escalating too quickly

It is far better to escalate too quickly, as long as you handle it right. Escalating too quickly is much less of a problem. But let me share two examples - one where I messed it up, and one where I did well first, but messed up at the end.

The first was a girl I met online. I flirted mercilessly, and made it sexual. What I did not account for is that girls often take things far further online than what they consider appropriate offline when meeting you. It is very easy for one party to treat online as fantasy, while the other treats it as a discussion of real-life desires.

We'd talked about me playing with her boobs online, and she'd promised to dress real sexy for me. She did, which reinforced my idea that she was available to me. She was a real bombshell, and arrived with sexy stockings, high heels, and a coat that somehow screamed "let me flash you".

We went to a cinema (note: cinemas are not good for a first date - they're fun once you've established enough attraction for groping to go on, or if you're actually there for the movie, not if you want to amp attraction), and I pretty much immediately went to touch her knee, then to put an arm around her.

She removed my arm, and I just assumed it was a bit of a game, and put it back a few minutes later. Repeat. The third time I put my arm there, she got up and stormed off. I followed her, whined about how she'd been all hot for me online, and we separated and never spoke again. She was genuinely angry at me for having pushed the interaction further than she was ready for, given that while we had talked quite a bit online, we had not talked much face to face yet.

Read her signs. Escalating quickly is fine, even when you mess up - some women are more than happy for very rapid escalation in situations where you have hit it off online. But I should have realized she was not ready, laughed it off, backed the hell off and started far down the scale and given her time before escalating again. Pay attention. If you want to move quickly, move with "small steps" so she can turn you down before you take things too far.

The other case was another girl I met online (this is how I used to meet all my women). She was new to town, met me for a drink, and we went to my office under the guise that she'd check her e-mail, and we'd goof off a bit.

She went on irc, asked me some question, and I went over and stood right behind her, and I just put my hands on her shoulders and started caressing her. It was like pressing a button. She spun around and pretty much threw herself in my arms, and we made out like crazy.

She was more than happy with rapid escalation. So far.

She sat on my lap, and I put my hand on her thighs, and pretty soon I slid my hand up and started rubbing the outside of her panties.

No go. She pulled my hand away. I just looked at her and grinned (good!) and went back to kissing her, felt her breasts a bit, and tried again. No go. I just grinned again, shrugged, and we kept making out. This time I backed off, sort of - I kept heating the rest up, but she had to go home to the family she was living with.

I walked her to her stop, and we made out a while longer, before realizing we were doing it right in front of a restaurant window. I was close to pushing her up against the wall (window) when we realized, and she went beet red. I just started laughing (good! Demonstrate you're not easy to intimidate), pulled her a little bit away, and made out a bit more and groped her ass.

So far, so good. She had to leave, but she was worked up like crazy (her panties had been soaked the first time I went for it).

Now, I did make mistakes, if my goal had been to get her in bed then and there and the logistics had been favorable, I'd been on the right track. But the logistics sucked, and we were not in a position to take it further. In that situation the biggest flaw I made was not pulling back and cooling down on her and made her having try to recover my attention to leave her wanting me more than I was letting on wanting her.

However, so far, relatively good for the most part. She was attracted. I had her number. She was beaming when she left me.

But regardless of my odds, I overplayed my card massively. Before we'd arranged a second date, I wrote her (guess what's coming?) a fucking love poem (uh oh).

I had met her once and I wrote her a long rambling fucking letter quoting an obscure Swedish poet (no, I'm not Swedish, but she was) and wrote her a love poem.

She never got back to me. I finally called her, and she gave me some bullshit excuse.

In closing:

Good ways of dealing with too rapid escalation:

  1. Back off.
  2. "Oopsie!" - make it clear you find it slightly amusing, and most certainly isn't embarrassed; you're just being a sexual man.
  3. Back the hell off. Read her signals. Work back up slowly.
  4. Pay attention to her signals as you escalate again.
  5. Keep trying, but don't be obnoxious and go straight back to the same thing.

Bad ways:

  • Go straight back to doing the same thing she refused you in the first place.
  • Show signs you were "caught out"
  • Go into overdrive: It's ok to take a step too far (going for the kiss when she's not there yet, for example), but not 2 or 3 or 4 steps. Writing a love poem, for example, as much as women love romantic movies and books, is more months into a serious relationship material than pre-second date material... And only then if you at the same time demonstrate that you're a strong masculine man, and the soppy stuff is just a passing weakness.