That all makes sense to me. The problem is that from where I am right now, these interactions are really awkward and difficult and that makes me want to avoid them. So that's what I need to push through. If I do, it should eventually get easier. I'm like a morbidly obese guy who needs to go to the gym, but doesn't want to because he knows he's going to consistently embarrass himself for a while. So much easier to stay on the couch.

Get off the couch. Start off talking with women that you have zero interest in and will never have any interest in. They will be easier for you to talk with because you won't perceive them as magical unicorns and hence you won't get anxious and stress out over the interaction. As you get more comfortable, talk with women you are 5% more likely to be interested in. Once you are comfortable with them, talk with women you are 10% more likely to be interested in. And so on. Or whatever progression works for you, as long as you are progressing. Same concept.

There is not some huge barrier out there for you to overcome. Just a lot of steps that you can take one at a time. Now go take the first step.

Or you could just take drugs.

I haven't been single in a long time but this seems like very solid advice.

I've never known how to acquire them, or I probably would. Not a lot but I'd definitely be up for the reefer and maybe give mushrooms a try. I listen to Joe Rogan's podcast and I get the feeling I'm missing out.

So it seems like things are starting to pick up. Last night I went to a bar that was having an event where Spanish speakers trying to learn English get together with English speakers trying to learn Spanish, while drinking lots of beer. I was the only gringo at my table along with three Chilean women and two Chilean guys. It was a dysfunctional setup at first because the women all came together, were all seated together at one side of the table, and were only speaking amongst themselves and in Spanish. But after a while one of them had to leave, and I made the bold move (for me) of moving to the vacant seat. After that the table was more of a cohesive chat, and incidentally I was now chatting with two reasonably attractive women, and we were all a little drunk. Although one of them was participating in the conversation a lot more than the other. Finally the more talkative one announced that they had to leave soon and I said (truthfully) that I should probably leave too, because I wanted to get home before the metro closed.

The place was in between two metro stops and it wasn't clear to me which one was closer, so I picked one direction and started walking, but they called after me and said they were going the other way, so I turned around and joined them. The talkative one was taking a train in the opposite direction but the quiet one was going my way. We got in the train together and she became a lot more talkative. Just before her stop she said she wanted to exchange phone numbers, which I hadn't been expecting at all. I was obviously fine with that, but since I'm still on a US phone plan and it's stupidly expensive to use down here (I should probably get a cheap phone with a prepaid plan to use while I'm here), I suggested it would be better if we contacted each other through Facebook. So we're Facebook friends now. I never had much of a use for Facebook before.

However, when I messaged her later that I liked her idea that the two of us should meet up occasionally to practice English/Spanish, her response was that maybe we'd meet at that bar again next week (it's a weekly event). So I'm not sure why she made that suggestion in the first place while we were on the train, or even why she wanted to exchange numbers, but whatever. The big takeaway for me is that since I currently have two prospects on the line (however tenuously) instead of just one, the mixed signals aren't putting me off near as much as they would otherwise.

You would probably be better served by focusing on improving your ability to interact with women in general rather than thinking of individual women as prospects.

Good move taking the seat and chatting them up. Keep doing stuff like that and try not to think too far ahead or develop expectations as to what will be next. Just enjoy the moment and focus on increasing your comfort level with simple conversation.

Not too surprisingly, she didn't show up tonight. She was at least a little drunk when she made the initial suggestion, regretted it when she sobered up, and then wanted nothing to do with me, that's how I'm reading this. As I said, not too surprised but I was still disappointed when she didn't show up tonight. So I responded in a way that is actually novel for me. I started hitting on the only available female at my table, probably in her early 20s and not even all that attractive, and I sent her a friend request on Facebook after getting her to tell me her name. For a while she was receptive but I think toward the end she was getting creeped out. I don't normally behave like this. No big deal I guess but as the alcohol wears off I'm starting to feel disgusted with myself. My ego was bruised and I wanted to see if I could drum up some female attention, that's all this was about. #desperate

A quick visit to youporn seemed appropriate. Ok done, time to get some sleep.

There are lots of reasons why she may not have shown up. "She regretted it when she sobered up, and then wanted nothing to do with me" is pretty low down that list. You're probably not that important to her. She may not care if she ever sees you again, but that doesn't mean you're the reason she didn't show. Maybe she was just tired.

Realize that chicks are just as horny as we are. Stop thinking that they are this mysterious unattainable object. Just be yourself and relax. Don't make it some do or die epic thing to talk to a girl and have her like you enough to give you sexy time. Instead go in with the mindset of hey, I just want to meet someone and have a good time. The rest will hopefully follow. If it doesn't move on and try again.

Also, at the risk of generalizing...I dated a girl in high school whose family was from Chile. They are reserved and conservative. They are not the stereotypical Latina sexpot. Maybe you should have gone to Brazil or Puerto Rico...those chicas are muy caliente!!!

Agreed that I'm probably not that important to her. I'm not saying she made a point of not showing up specifically because I was going to be there. I just think she may not have had any intention of going back in the first place, and only said "maybe I'll see you there next week" as a way to back out of her earlier suggestion that we arrange to meet separately from the group (ie "intercambio"). Between my interaction with her on the train and her later text via facebook, she had definitely reassessed the situation. She did comment while we were talking on the train that she was really drunk, so that might have something to do with it. I do realize though that further analysis isn't going to get me anywhere and I need to let this drop.

If I did meet someone who was hypersexual, I'd just be intimidated, so Chile might be more my speed. I'm not entirely clear on what I want though. Obviously I was pursuing the girl last night because at least on the most basic level I wanted to have sex with her (even if I might have vetoed it as a bad idea if the opportunity had actually presented itself, as I've done before. Lots of internal conflict going on with me. I'm a mess.) What I really want, or at least what I believe I want, is a relationship. I certainly wasn't expecting the situation last night to ever lead to a relationship though, so sex was the only logical motive for me to act the way I was acting. But my behavior in this area isn't logical at all.

I've got three women including the one I was bothering last night as facebook friends now, and as far as I can tell this all leads nowhere. This hasn't stopped me from compulsively checking facebook throughout the day waiting for something to happen though. At least I'm making an attempt to put myself in the game? It's better than nothing? From where I'm at (41 year old near-virgin), almost any change in behavior patterns has to be regarded as a positive, and I've definitely been acting... different. I had a consistently negative outlook on life before I came down here, and now I'm putting myself in unfamiliar situations and feeling unstable. Seems like an improvement.

cool blog.

you need a life coach.

That will be easier to find in the US, good luck and become positive.

It goes without saying you want a committed relationship with a good looking woman. What other qualities are you looking for in a woman? Seems like you enjoy outdoor activities so that might be something you can share with a woman. I'm not meaning to be harsh with this but I think it is fair to say that you have a hard time making commitments period. If you are looking to have a committed relationship with a woman having a hard time making commitments to anything is a problem that needs addressed first wouldn't you think?

Have you considered a woman in your own age range. You seem to be targeting these younger women. I'm about the same age as you (I'm 39) and I really can't imagine relating to a woman who is in her early 20s. I'm sure there are plenty of women over 35 that you can get. Maybe you should become a schoolteacher or a personal trainer...seems like a good way to meet some middle aged divorcees.

Seriously, I am rooting for you.

I'm in Viña del Mar for the weekend. There's a casino here, and as far as I know it's the closest casino to Santiago that offers poker, but tbh it kind of sucks. They don't even start playing poker until 6pm I think, and the last time I was here and arrived at the casino at 6pm we still had to wait at least an hour for enough people to show up before any hands were dealt. Last night I got here late, there was a game running but the table was full, and after waiting a while for enough people to show up to start another table I just gave up on it because I was tired. So if you're interested in going somewhere to play live poker I can't recommend Chile at all. I'll probably give it another shot tonight though, just because I can't think of anything else to do. I almost took a bus back to Santiago this morning but that felt like I'd be giving up on my poorly planned weekend trip to soon, so I'll give it another day. There's probably a club scene here in Viña but that doesn't interest me at all.

I can accept that I need advice from people who are good at life, since I'm struggling with mine, but I'm highly skeptical that a "life coach" could help me. Or maybe 1% of life coaches would have some real insights to offer but if I can't identify who's good and who isn't, that doesn't help. Life coach, therapist, or whatever they choose to call themselves, the title doesn't matter much to me. I think my circumstances are really unusual and it would be hard for me to find someone who could both relate to where I'm coming from and offer useful advice that would help me get to a better place. So for now I'll see what I can get from the readers of this blog. And then I'll ignore most of it anyway.

I've gone so long with the attitude that any woman I would want would be unattainable to me that I haven't really put a lot of thought into what qualities I'm looking for! In reality if she's attractive and not obviously stupid or a complete bitch, that's enough for me to be interested in a "please marry me" kind of way, and also enough for me to have the conviction that she'll lose interest once she gets to know me (the root cause of which is that I don't respect myself, so that's where I think the work needs to begin). From there it's all about how long I can trick her into thinking I'm acceptable. Maybe I'm exaggerating a little but that's my general psychology when it comes to relationships, and probably the main reason I've never been able to maintain one. I don't think I lack the ability to commit to a relationship though. When I meet someone I like, I pretty much want to get married right away.

But the younger ones look better! My ideal age range would be 25-35, although 25-30 >>> 30-35. Even I think it's weird that I'm pining for a 21 year old though (yesterday she liked one of my facebook statuses!). But ok, the women I've fb friended over the past week are 21, 24, and the other one I'm not sure but I'd be surprised if she's over 25, so there's definitely a pattern here. I bet if I had some experience in relationships I'd be less interested in these inappropriately young women, because they're probably annoying after a while, but I never get very far beyond surface level interaction. So that's part of it. And then maybe because I'm emotionally immature I tend to attract them. To be honest, the main thing I'm getting out of it right now is an ego boost, although that's wearing off since it's been a while now since I interacted with them and I'll probably never see any of them again. And then I can go back to ignoring facebook.

And she just posted that she's in Valparaiso, which is very near to Viña where I'm at, so I liked her status. Fb likes are the most chicken**** mode of interaction ever. Going out for a run, then back to my room to check fb (since I have wifi here) on the slim chance she messages me, and then if not I'll get some dinner and off to the casino again.

Yo so what's new? Need update, it's been over two weeks. I'm in a similar situation now, and will likely start flying to foreign lands for months at a time in the next few years. The best thing I've done for myself is getting into a regular gym program. The second half of my 39 years were spent doing everything that's not healthy, so it's been amazing to feel healthy and look good again. Helps a lot with depression and confidence.

More nonsense along the same lines, but I guess enough of it has accumulated for another post. First let me reaffirm my anti-recommendation of the casino in Vina del Mar. After my last post which was on a Saturday I ended up going there again (after 6pm, because remember the schedule states they don't even start offering poker until then). The previous night I had waited for another table to open up before giving up on it. This time, Saturday night maybe 8pm, there was no poker game going at all. Definitely won't be going back.

Not surprisingly, nothing came of that. But last week she liked my fb status where I mentioned that I finally got a cheap prepaid phone through a Chilean carrier (I wasn’t reachable by phone here previously). Then I posted another fb status after finding an outdoor ping pong table in a public park near my apartment, asking if anyone wanted to play. She replied that she’d like to and that she lives nearby too, so I responded that other than the Spanish class I have in the morning my schedule is open and if she wants to name a time I’d probably be up for it, but then she never got back to me. I don’t know what’s up with her really or why she periodically shows interest in me, then stops, but I’m tired of thinking about it. It has become a pattern now and if it’s designed to drive me crazy, she’s doing well. I won’t be initiating any further contact with her. I almost think she’s trolling me at this point. Actually I have another theory and there’s more to the story, but I’ve written enough about this and anyway I’m just trying to forget about her now.



Re: Forgetting about her. I’d like to meet someone else, so I created a Tinder account two days ago. So far I’ve only found one match (35, recently divorced with 3 kids, and I’m not particularly attracted to her) but we texted yesterday and she says she’d like to meet me this weekend. If that actually happens I’ll post about it here.

I don't really like wine, but every once in a while I give it another chance and reconfirm that I don't like it. (On the other hand, there's some kind of a drink they have here in Chile which is served hot, has wine and cinnamon and orange slices and I'm not sure what else, maybe something to sweeten the wine a bit, and I really liked it, even though the cinnamon made me cough the first few sips. It's called Navegado.) So anyway I had a bottle of wine that I'd only poured one glass from a few weeks ago and was about to pour the rest of it down the drain just now, but at the last minute I decided maybe I'd get drunk tonight instead. Feeling depressed and haven't done much drinking lately, so why not?



The Tinder experiment went nowhere. As I posted earlier, I had one match and she eventually texted that she'd like to meet that weekend, but then when I asked what day/time would be good for her, nothing. Two more matches popped up, and one of them also indicated she'd like to meet, with the same result when I tried to schedule it. Exactly what I've come to expect from internet dating. Of course I could keep trying and eventually I'd meet someone but right now my confidence is so ****ed I don't even want to meet anyone, so I'm done with it at least for now.

The other thing that happened is my fault. Bob and I went to an event at a bar where he ran into a friend of a friend (Laura), and the three of us ended up going to another place that was more quiet where we could talk. I didn't want to talk much due to the aforementioned confidence issues, and I especially didn't want to talk about myself, but Laura made an effort to get to know me so eventually I opened up a little. Somehow, even though I was really gloomy and pathetic in the way I presented myself, she seemed to like me (while I wondered why she was still talking to me).

So Laura and I became Facebook friends and a week later she posted that she was offering individual Spanish lessons, which of course caught my interest. "I'm just inquiring about the Spanish lessons, that's it. If anything else happens great, but that's not what this is about. I'm not going to make it weird." Having told myself that, I messaged her and we scheduled the lessons, starting in June. Then later that night she texted me: "Let's talk." Of course I was happy to have her texting me, but also terrified because I couldn't think of anything to say. After several long pauses I ended up texting lame and unnecessary questions about the Spanish lessons even though it was pretty clear she was texting me on a social basis and after answering a few of the questions she stopped responding.

But later that weekend (last week) she invited me to an event she was attending. This was some kind of a networking event for locals and expats, not something I would normally attend, but since she invited me I decided to go. When I got there I walked past her, but it seemed like she either didn't recognize me or didn't want to interact with me because she just kept walking and went to talk with some people she knew. This really threw me off, and instead of approaching her I went to a corner of the room and played games on my phone for a while, then left early because I felt so uncomfortable. A few days later she texted me to ask if I had been there, because she thought she saw me, but when she went to look for me later I wasn't there. I texted her back that yes I had been there, but I left early so I could catch the metro back to my apartment before it closed. So that's where things are at now. Guess I'll see her in June but it seems I have made things weird.

Next time instead of asking where and when is good for her try something like, "let's meet up Thursday at bar X at 7:30." makes it simpler since all she has to say is "sure, see you then." if that doesn't work for her then you can figure something else out. plus you seem more confident if you suggest a place/time to meet vs asking her to decide.

It's best for the man to initiate, right? I rarely do and it's got to be at least some small part of the problem. Since I don't know the city very well I was thinking it would be better at least with local women if I let them make the plans since they would have specific places in mind and know how things are done here, but overall that's probably a mistake because it requires them to initiate and makes me look unconfident (which I am, obviously a major problem as well). I'd get better results suggesting specific plans myself, even though I'm less familiar with local venues. I'll try to do that next time. I had been thinking this might be an issue and your post gives me confirmation.

Welcome to a Very Special Episode of my blog! I’ve been having an internal debate for a while about whether or not I should post this, because it’s an issue that’s very difficult for me to discuss, but I’ve decided to post it here because it was a formative experience and it happens to be highly relevant to the issues I’m trying to deal with now. Something terrible happened to me when I was 11.

Well ok, let me unpack that a little before I go on. The psychological impact of what happened was absolutely devastating to me. From an adult perspective, I can look at the incident now as something that was very unfortunate, especially having it happen at that age, but not really the end of the world either. I wish a sympathetic adult would have been there to talk me through it back then. With proper guidance it seems like I could have come through ok. Unfortunately, even though my parents provided me with a stable environment, the emotional connection was lacking and I never felt like I could talk to them about anything beyond routine surface level stuff. So as it was, I kept this incident to myself and I went through my teenage years with the underlying belief that nothing I did mattered because my life was already ruined, and that I should kill myself.

Enough preamble. What happened on the playground when I was 11 is that I caught an elbow to the groin while playing a particularly rough game of "touch" football. I passed out and when I eventually came to, I was sweating a lot and I was nauseous for the next hour or so, and my memory isn’t entirely clear on this but I seem to recall that the next time I pissed it came out strangely thick (I didn’t even know what semen was at the time) and a little bloody. That was about it though. By the time I got home I probably felt a little sick still but I could manage, and anyway I didn’t want to talk about it. At school the next day the incident seemed to be forgotten, and that was fine with me.

But later I noticed that my left testicle looked weird and misshapen, and it would ache periodically in a way that it never did before. This turned out to be permanent. Much later, when I finally went to a doctor to have it looked at when I was in my early 20s, I was told that what I had was a varicose vein and that I could have surgery for it if I wanted, but it was nothing particularly serious. I elected to have the surgery (mostly for cosmetic reasons though it still looks weird to me) and at that point had to tell my parents something about what had happened, so I told them as little as possible and I don't think they really wanted to know about it anyway. Unpleasant stuff, move along, nothing to see here.

So medically this was all pretty mundane, but psychologically it was another story entirely. I kept everything to myself during my teenage years and I assumed the worst. I was convinced that no woman would ever want to sleep with me, at least not if she knew what had happened, ie that I was completely ruined as a man. Maybe I could try dating, but what was the point? It could never go anywhere. So I didn't date. A few girls showed some interest and I would ignore them.

Fast forward to now and it's probably obvious if you've been reading the blog, but I still have significant unresolved issues from this. I've had sex exactly once in my life, with a prostitute in Amsterdam maybe 15 years ago. It was not a pleasant experience, and I was so nervous I didn't even come. But technically I'm not this guy:



That would be a seriously dark movie if they wanted to delve into the psyche of any guy who might find himself in that situation though. I don't think anyone reaches that point in life without serious trauma of some kind.

Medically apart from the cosmetic issue I'm basically ok. I'd want to explain my situation to any woman I was going to sleep with, but there's no physical reason I couldn't have sex. Psychologically I'm a mess, of course. The only way I could see things ever working out for me, would be if I was in a relationship with someone I could trust enough to open up to fully. That's going to be extremely difficult. I might as well at least try, though.

I think I can promise that this is as heavy as this blog is ever going to get. Maybe the next entry will be funny or clever or entertaining.

Steve, women don't care about your balls. I'm very confident that no woman would even notice any minor cosmetic issue with one if your balls.

Based on what you wrote I'm not even sure what the cosmetic issue is after the surgery. How weird does it look? It's only the one that was affected right, so you still have at least one fully functioning testicle?

I don't see this as a major hurdle at all. I get that you are awkward around women and find it extremely difficult to start relationships with them, but if your balls have anything to do with this it is figuratively, not literally.

If insecurity over your testicle is truly what's been holding you back, then 100% get over it. It is a ridiculous thing to worry about unless I'm missing something important in your story. Assuming it is a superficial problem, as I said before, no woman will notice or care. Unfortunately I suspect your lack of confidence around women is rooted much deeper than this, and maybe you are rationalizing your situation with this misshapen nut narrative.

It really is a major thing holding me back, and I get that it may be almost entirely a psychological issue at this point, but I don't think I'm rationalizing or using it as a cover story for something else. Insecurity over the possibility of a woman being horrified by the way I look naked has prevented me from having sex. Or even if she commented on it at all I'd have a hard time dealing with that. If it weren't for this issue I would at the very least have had occasional casual sex throughout my life, even if deeper issues continued to get in the way of my ability to have relationships. It hasn't happened very often but over the years I've had a few clear opportunities, which I've passed up on and/or sabotaged due specifically to this issue. I'm not saying my fears are at all justified (I have no experience through which to judge whether they are or not), only that these fears exist and have led to me being terrified of sex.

I can either get over it or I can accept that my life isn't ever going to include sex. So yes, I need to get over it. You asked about the physical appearance of the affected testicle (an entirely reasonable question under the circumstances). Sometimes it appears almost normal but sometimes there's a "bag of worms" appearance (even after the surgery) which is typical of varicoceles - that's what I was referring to when I said it looked misshapen. I think it hangs lower than the other one by more than it should. It seems entirely plausible to me that this may not be such a big deal, and if I had to guess it probably wouldn't be for most women, if they even noticed it at all. But what if it was? It might sound silly to you, but this is genuinely a major hurdle for me.