My new dating strategy (which also won't work)

Seconding this.

This may sound a bit strange, but my best relationships have been with women that I wasn’t that interested in from the get-go (not saying that the approach will get you an instant relationship, but still). I’ve mentioned this before in other threads, too.

The reason? If I’m heels-over-head about someone, I’ll be drooling on my shoes, and I’ll generally be behaving like either a nervous wreck or a crazy stalker.

If I feel more like “I could take it or leave it”, I’ll behave a lot more like a normal person.

I’ll be honest: At this point, when it comes to potential dates, I’m basically mentally filtering out the women who press all my buttons and make me go “wow” just as quickly as the ones who completely turn me off. Because I know what I’m like when I’m around someone that I like too much.

Indeed, but the OP needs to start off with baby steps. One needs to learn to doggie paddle before doing the breast stroke (or, stroke breasts for that matter).

OP should ask out anyone he thinks is cool, but only those virtually guaranteed to accept his offer. He needs to learn the ecstasy of having women accept dates with him. Only later does he need to learn the agony of defeat.

So, I recommend that he go down to the memory care unit of his local skilled nursing facility and seek out all the single women on the Alzheimer’s corridor. Trust me, these can be some very fun, feisty and forgetful (what happens in Alzheimer’s unit, stays in Alzheimer’s unit) gals!

He’s assured that these ladies will accept his date request—in fact, they would probably even accept a date from a mop.

Afraid your facility-date may overextend your bank account? Au contraire! Can you afford Jello l’Orange? Chateaubranflakes? Yes, of course you can.

Sex? Yes, it’s not out of the question, you know. These old dames have been around the block a few thousand times to be sure. Just be sure that they put on a fresh pair of Depends® before you go out and that they remove their dentures before engaging in any “oral pleasuring” (I learned that lesson the hard way).

It’s not just doing it enough. It’s doing it right. Light and casual and preferably with a hint of wit and aftershave. Otherwise it’s just a series of failues that builds on itself and destroys confidence.

This. The process is not:

  1. meet woman you think you might like
  2. get to know her
  3. decide you’re in love with her
  4. ask her out
  5. date, get married, live happily ever after,

it’s:

  1. meet woman you think you might like
  2. ask her out
  3. get to know her
  4. decide you’re in love with her, continue dating
  5. get married, live happily ever after

If you wait until step 4 to ask her out, by that point, you’ve built up a big fantasy success scenario in your head, you’re extra nervous because this is the one so you come across as a sweaty geek, you’re devastated if it doesn’t go well, and it’s practically guaranteed not to go well because women are put off by guys who they thought were just friends but who have been secretly falling in love with them without their participation.

You’re going to say it’s a waste of your time to ask someone out without really knowing she’s who you want to date. This is not only counterproductive (steps 2 and 3 can be fun even if they’re not “the one”), but not even true, since you’re currently wasting all your potential dating time with a losing strategy that’s just turning you more and more bitter and undateable.

I think this is a GREAT point. Not being female I can only base what I think on what I’ve observed (as opposed to “actually having felt”) over the years, but I think this person has hit the nail on the head: confidence, without seeming needy, clingy, or desperate, is what can win you the MOST points with women. That can be a tough little balancing act but if you can pull it off you should have NO problems attracting just about any woman you want (although a good sense of humor - which the OP says he has - can’t hurt. One of my wife’s sisters long ago told her that “I’m a sucker for any man that can make me laugh.”).

Decent guy I know used to sound a lot like you. His CBT therapist gave him a mission: he had to ask 10 women a month out on dates. That was all. He could be a total weirdo doing it, they could be strangers, they could be his best friend, the therapist didn’t give a shit. 10 women a month.

And the first month (IIRC, I’m kind of extrapolating from vague memory here) was agony. He was such a weird fucking cringing creepo, apologizing as he asked women out on dates. 10 rejections.

But by the second month, honestly, it was getting a little boring. He ended up being surprised when a couple of the women accepted. And he went on a couple of pretty dead-end dates.

During the third month, he was getting used to it, no longer such a weird fucking cringing creepo, and went on a few more dates, and ended up meeting a woman he really clicked with.

What was holding him back was the huge stakes he was putting on every date, so he approached dating like an appointment with the oncologist. By the 30th date request, he’d realized that rejection wasn’t actually a big fuckin deal, that he’d survive it just fine, and so he came across as a funny, witty dude instead.

I’m not your therapist. But I thought that was kind of brilliant.

Edit: in case you’re wondering, this ain’t my story. I backed into every relationship I’ve been in, including my marriage.

Look, OP. You can continue to be super selective on a slow burn while making minimal effort. The world won’t end. You can feel good about “being you.” If that’s what you value most, you can have that. But life is about trade-offs, so recognize that you are making a choice every day that affects your chances of finding a partner.

Confidence is not some arbitrary hoop women love to make men jump through. People like confidence because confidence is better. Confident people are more fun to be around. They make more friends. They make more money. The are more successful at what they try to do, and they bring success to those around them. If you don’t want to cultivate that, that’s fine. But it will hobble you. I’d suggest getting over yourself, or else finding one heck of a way to compensate.

People do not want to date people who are already super emotionally invested. It’s not flattering, it’s anti-flattering. Nobody wants to be a prop on some fantasy you’ve already made up in your head. They want a partnership, a give-and-take, a thing that grows proportionally between two people with delightful anticipation and escalation. When you over-invest, it stops being about the actual woman and starts being more like some book you are casting a role for. It’s creepy and unfun. It makes women feel generic, Interchangeable, and like a stand-in to whose opinions and emotions don’t matter.

Do whatever the hell you want. But millions of people poorer, uglier and less fun than you manage to find happy relationships. Cutting out a few pieces of self-defeating bullshit will help you get that, too. Or, you can just ignore us and keep doing what you are doing.

That’s the plan.

What’s the plan? Most of what even sven said?

In that case, good! Since it’s the exact opposite of the “plan” in your OP.

Or did you mean this?

In that case… Well, best of luck to you with that, I suppose.

I just thought of another incident from my past that can perhaps shed light and help the OP to reassess his feelings about what women actually appreciate in a man (hint: they don’t respect touchy-feely, mealy-mouthed Dudly DoRights).

I may have mentioned before that I grew up in South Jersey, where men are goombas and women are men. I kid (not much), but, Jersey girls do have a certain “in your face” attitude toward life in general and men in particular. Let’s just say, you don’t want to mess with Jersey chicks unless you’re wearing a titanium groin protector.

This took place before I “broke bad” and was still intimidated by women and scared to ask them out on dates:

One night, decades ago, my friend Ernie and I walked into a popular nightclub on Long Beach Island at the Jersey shore (The Clam, Beach Haven). As usual, I scoped out the joint, located a couple of fine female specimens and told Ernie that we needed to sit next to them at the bar—and we did.

The girls were very cute and just my type when I was in my early 20’s: skinny, loud, big hair, Italian.

This was the era of Disco music and the house band was playing one disco song after another (mostly Bee Gees). I kept trying to muster the courage to ask the girl now seated next to me to dance. That was my designated girl; Ernie would have to make do with the one seated next to my girl—she had an enormous nose, a cockeyed mouth and complexion problems. But, Ernie was no Adonis, so he was happy to deal with my scraps. The whole mix-n-match depended on me getting up the nerve to ask “my” girl to dance and only then could everything else fall into place.

But…I wimped out.

I kept blaming it on the song selection, but the fact was, I was just too scared to ask the girl seated next to me to dance. Ernie kept nudging me into action, but I kept waving him off…”next song, I promise.” I kept glancing at my girl, and she kept glancing at me. I could tell she was interested in me, but still, I was afraid to put my heart/balls on the line. All for a stupid dance?!?

This timidity went on song after song. At one point, “my girl” asked me for a match (yes, kids, people used to smoke in the old days) and I handed her my book of matches. But, that’s all I gave her…no invitation to talk or dance or anything else. I was a mute, imbecilic gelding, so to speak.

I was ashamed of myself. I should have asked this girl to dance and then get to know her better. I wanted her; she appeared to want me; Ernie wanted the big-nosed friend; the big-nosed friend appeared to want Ernie. It was all up to me to make this sexual smorgasbord come to fruition. But, I dropped the ball. My *“nice guy” *persona got the best of me and I acted like a heterosexual amongst a cornucopia of homosexuals; or a homosexual amongst a cornucopia of heterosexuals. Bottom line: I was a testosterone-depleted pansy.

Then, when a particularly awesome, bass-driven Disco masterpiece started thumping from the subwoofers, I finally mustered the courage to ask my gal to dance.

But, alas, it was not meant to be. When I looked over, the lust of my life was standing up, along with Big Nose. She slid her hand toward me on the bar, then she and Big-Nose walked out of the disco facility, never again to be seen by me or Ernie. I looked down where she had slid her hand and there under my nose was the book of matches I graciously gave her.

I picked up the matchbook and looked at it. I was shocked. My potential immortal beloved had removed all but 5 matches in the front row of the matchbook; and all but the middle match was bent backward. The message was clear. On the inside flap she wrote, “I would have said yes, asshole.”

That was yet another brick in the wall of my discarding my “nice guy” façade and becoming what women really want.

Fifthed I think. The first time I asked my wife out I wasn’t even that interested in her. I did it partially because I didn’t want her to be stuck going to see the G&S operetta her friend was playing violin in. It was also a low stress date - just skating at the rink a few thousand feet from the dorm. And she was leaving to go back to her school the next morning.
But it turned out that we hit it off. You can never tell unless you give the relationship a chance to develop naturally. When you succeed with anybody you know what to do with those you might be more interested in.
Plus, fake confidence builds real confidence.

I was engaged before there was an internet, but after some low stress online interaction the woman won’t be a stranger any more. Plus you have the benefit of thinking about what you are saying more than you can face to face. If it develops into a date she’ll be coming to it with a positive attitude about you. On-line you can fake your picture, you can fake your age, you can fake your resume, but you can’t fake how you interact, not for long anyhow.
Back when I was in college and only about 15% of the students in my school were women, we met through mixers, where you asked a girl to dance, talked with her, got her phone number if you clicked, and then asked her out with a fairly high chance of success. I bet the woman you ask out on-line is less of a stranger than the women I asked out after a mixer.

We’ve met IRL, etc. That doesn’t mean I know you, so take this with good intention.

You’ve got a lot going for you.You’re personable, intelligent, have a good sense of humor, and have reasonable social skills. You can go with the flow, and are willing to put yourself out there. These are huge advantages.

You’ve also gone through some shit the last couple years that was distracting, probably put dating on the back burner. Now that other things are more aligned, you can work on dating. Those also make you more dateable.

There is no silver bullet, and there’s no guarantees.

Just like you were able to beat everything the last couple of years, you can beat this, too. You know what needs to be done. You just have to make up your mind and do it. Sitting around feeling sorry for yourself ( even if justified) ain’t going to cut it. And it’ll be just as hard as what you’ve gone through already, probably harder. You’ve got a lot invested in the idea of who you are, who you present to the world.

You have to decide what is more important, dating, spending your life with someone, or listening to that same old monkey in your head, lying and saying “I can’t”

You’re a good guy, Jim, and I’m rooting for you.

My random dating analogy:

Imagine reading the SDMB if you really really really REALLY wanted to read threads, but would only open a thread if it had a perfect title, and only if it was on the front page for three days, and only if it had 40-85 responses, and only if the poster who started it had a username with over six letters and no numbers, and only if on mouseover it made you laugh until you cried.

You wouldn’t be reading much, and when you picked a thread, you’d want that thread to be amazing.

That’s what it sounds like you’re doing with dating.

People aren’t dope threads, but we’re similar. Some good threads have terrible titles. Some threads will draw you in if you give them a chance. Some you can interact with and find you really like them. Some sound awesome but are just stupid. You can’t really know until you read a thread. Even the ones started by trolls and fools can be hilarious and fun.

And if you aren’t enjoying one? You don’t have to read to the end. You hit the back button and you go back to what you were doing.

As for rejection: I was at a party last night where the waiters were circulating with food, some that looked really great but that I couldn’t eat and some that didn’t look all that appealing. So, they’d ask if I wanted something and I would say no, but they didn’t know why I said no.

And neither do you.

But if you send an email like the OP? Well, then you can be certain why. I guess that’s something.

Well, your approach gets points for eliminating the fear of rejection, at the expense of having poor Boyo Jim ask dudes out on dates. I’m going to have to mark that as a fail.

What has always worked for me is just being genuinely interested and attracted to someone. It is not as if I never get rejected, but I have also dated lots of women I am genuinely interested in and attracted to.

I gave up online dating, at least for now. My last 2 relationships came out of that, and in both cases something seemed to be missing after awhile. That’s just me, maybe it works for other people. It does seem to work just fine for getting laid, but I guess I want something that will last and have it in my head that I will pick up things in person that I will miss on line.

I think the OP is somewhat handicapped by his rejectionphobia. Maybe counseling really is one answer, or maybe just some self-inquiry into what this response is all about and how to control it. The phobia seems to be hijacking his behavior and introducing himself to women instead of Boyo himself, kinda like a modern-day demonic possession, only without the green foam and the head spinning around 360 degrees. I don’t think Boyo is the problem, I think his fear of rejection is tripping him up.

Wait. Have we ruled those out the OP’s case? Because that would explain a lot of the rejections he’s getting.

But it transfers. If you don’t like yourself and advertise that fact, you are telling women not to date you. And if other people see good qualities in you, that transfers socially.

Dude, I think you’re doing it wrong. I don’t think you know how to ask a girl out.

You don’t EVER say (or write), “Would you like to go out with me sometime?” That’s not an invitation, that’s asking for a wide open commitment to do God-knows-what, God-knows-when. Why would a girl agree to that? And, as you’ve found, a typical response is, “No, thank you.” Who wants to hear that she NEVER wants to see you?

The way to ask for a “date” is, as the name implies, to offer an invitation for a specific event at a specific date and time. “Suzy Floozy, I’m calling to ask if you’d like to see the Beatles cover band with me this Friday.” Suzy knows exactly what she’s committing to, or refusing, and she’s free to counter if so inclined:“Sure, I love the Beatles, what time?” or “Gee, I can’t Friday, Saturday would work for me, though.” (Then you say, “Nah, I’m busy Saturday.” Just kidding! Take Saturday!)

Plus, if you get a, “Sorry, I already have plans,” who says that’s a rejection of you? Maybe the girl is busy. Call her again a month later. (Then stop. Two refusals without a counter means she’s not interested.)

Asking a girl to “this Sunday’s matinee” sounds like you’re looking for someone to go see a movie with, asking her if she’d like to “go on a date sometime” sounds like you’re looking for a girlfriend.

This is “spot on” and the best advice yet. I read this and then I was thinking back to every lukewarm date I ever went on when I was in my 20’s and I realized that THIS is the defining factor. If these guys had asked to join me for a cup of coffee I probably would’ve hemmed and hedged and put them off, but “Hey Ann, someone just gave me 2 tickets for Cirque De Soleil tonight, wanna go?” just sent my head in a different direction – not so much “Gee, I know Gene has a little crush on me and maybe I shouldn’t encourage him” but “Cool, I’ve heard great things about this show and I’d like to see it, I can deal with hanging out with Gene for a little while.”

Try it - this is the best advice yet.

So you got to see Cirque De Soleil for free. I don’t see what was in it for poor Gene, who probably thought that you liked him.

Don’t get me wrong, it’s still good advice to the OP. Or it can be. But not for this reason. Or at least not exactly.

(Well, unless Gene ended up getting laid. In which case, what the hell do I know?)

Anyway, if you’re getting the vibe that someone more or less likes you to begin with, I don’t see why asking them out for coffee has to be a bad thing. You don’t have to buy them off with front row tickets to the opera. In a lot of cases, I think that would be more off-putting. “Why is this guy offering me that front row ticket? He barely knows me.” That could be seen as coming on way too strong too soon. Also, what if she doesn’t like opera?

“Want to get some coffee?” is more casual and less all guns blazing. Although some specificity concerning time and place is probably not a bad idea.