Advice: Deflowering a male virgin

I’ve been looking for this video for years. Unfortunately I don’t have any female friends whether work or school that I’d feel this comfortable with. Actually comfort isn’t the word, the women I’ve known and maintained friendly contact aren’t the types of women I’d have any sexual attraction for.

One I’ve known since high school is married and knows of some of my issues with women especially in college. Another one who I’ve been talking to since my days at Mission College really isn’t my type and I’mm glad to count her as a friend, however, she often leans on me for relationship things. Anyone else I’ve maintained contact with either aren’t very attractive or perhaps a little too old etc.

I suppose if I really maintained contact whether through school or work with any attractive women I hope that it would be a subject she would be willing to listen. Of course she has to be comfortable and I have to be open about my desire. So whoever wrote Max on this subject was very open to deflowering a man otherwise she wouldn’t have even asked for advice.

With this being said, I’m glad I found this video and from what I recall Max suggested the lady should go for it. Perhaps they have by now since the video is eight years old.

Facebook dating?


I’ve spent about a week playing with the new facebook dating thingie. I’ve had a few matches already however not enough conversations. They jury as far as i’m concerned is still out as far as whether or not this is worth it.

I will add that since I’ve been on facebook since before it became a big deal and back when only college students largely populated the site I’ve been using the site to check out women anyway. I largely approached the site in that vein alone in addition to connecting with people I knew from before I got into Mission College.

Of course in this case I won’t just be checking out women who were my contemporaries at the neighboring universities in the area where I attended school. I will be scoping out women in the Chicago-area and hoping to make a match. Like I said I made quite a few matches though I could hardly characterize those as solid nibbles.

What I may not like since I’ve largely become vain about my age is how it’s put on your dating profile. Like I do with Tinder or even Bumble I should be able to leave that off. Perhaps I should suggest that to Facebook Dating. Also at least with Tinder you can reverse any likes or dislikes (or reverse your acceptance or rejection while swiping).

Either way I do like being able to be very selective about who you would want to match with. Let’s say you can set your filter to whether or not your potential matches has children. I could utilize that more often to be honest and not just that attribute of course.

Another thing I’ve done is pick nine women off of my facebook list that would open the door do some interesting crushes. I’ve debated whether or not they know that they’re my secret crush – which could help thin the pool of available women presuming they are single. One just for the hell of it is one I’ve been talking to since going to Mission more as a friend than as anyone I’m interested in alas. Others are from the sister school Hillman College, some live in the Chicago-area, one I used to work with, etc.

I’ll update you if I let any of these ladies know of my crush on them. And even better I can always make changes to the list so the first nine I have, may change in the future.

BTW, I got to wonder what Tommy thinks of this new facebook dating. Will he ever do a review of it? He has been very quiet lately…

Is a Late Bloomer Allowed Bad Choices…even if on Purpose?

I also consider myself a “late bloomer” and I think you’re allowed good or bad choices. I wouldn’t make the same decisions that “Dateless Man” would. Then again or would I?

My bad choice when it comes to women would be regarding youth. I’ve explored being a so-called “sugar daddy”. Except that I don’t make sugar daddy money so the odds of that is very low. Regardless having been an older student at Mission College among younger students, especially female students I’d still want to thing I can handle this.

Also, I’ve worked with younger women and still do at a grocery store. I’d entertain it although I know that I have to deal with immaturity. No matter how I could relate to women who are say of college age at least I have to accept that yours truly would be too old for them.

So I may judge Dateless Man’s choices, but if he feels it’s worth giving someone who isn’t his type an opportunity he should. I may not do that so easily, however, I have my own wants when it comes to women.

What do you think?

The New Adventures of Dateless-Man!

Once again a month has gone by without another installment from the Dateless-Man. It seems to commonly happen around the summer for various reasons; I’d been faithful about typing up at least one post a month since July 2018, when I’d missed that June. Granted, that was also the month where things regarding my still unresolved eviction battle with the slumlord started to hit full steam. I am pleased to see so many new readers are checking out what I usually dub “My Lonely Man Blog.” While most of you are from the United States, WordPress’ tabulators are detecting hits from Canada, the U.K. and even India! I guess it shows that some of the issues I have are truly universal for some men, and people in general. Anyway, we’re more than midway past August so I’d better whip something up now!

As much as it is difficult to focus…

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Psychology: Sociopathy

yellow bokeh photo

I know that I had spend just about a year “whining” about my old hustler. Also in talking with others about him I’ve run into a term that more than likely I just have gravitated towards, “sociopath”. Sometimes I have to remember that I’m not a mental health professional, and I have to stop myself from wondering who else had I run into who might have been a sociopath.

Doing that would just continue to drive me nuts and place me deeper within the kaos.

What have I written about since writing about trying to have rules of no engagement with Anthony. I’ve had the greatest period of peace in my life since I have met him. Think about this after he made some of his moves when we first met at the theater, I started off avoiding him because he came at me right away begging. Also he was the type that would let me know I had a crisis and really try to drive home that he was trying to avert this crisis.

His questions and comments about me being a virgin, I’ve decided was an attempt at an edge. He wanted me to think of it as a bad thing and it’s something I must address before a certain point before it becomes a problem. It’s probably not really an issue for him since he seems to have little issue getting any – he loves to chase p@$$y although he seems to be perpetually single. What I’ve begun to theorize since I’ve known him is this small piece of information to him means I have some value to him – i.e. money at his beck and call.

I often say that my current rules of no engagement might well bother him. He may not entirely know why I’m just not answering the phone for him. He may not understand my lack of urgency as far as his voicemail at the end of last year. Then again he might realize that I’m trying to cut ties, perhaps he knows “my game” and since that wasn’t part of his plan he’s probably trying to get me back onto his planet.

His motivations for “befriending” me years ago is clear to me. I realize that our conversations about life or business was empty – and as far as yours truly I suspect Anthony considers anything I say about life to be empty. I realize most of them time we would ever talk it often could lead to him asking for something. And now if he can keep the lines of communication going it’ll happen again because that’s the pattern.

So while a few months ago I showed a video actually of psychopaths and have used sociopath or sociopathy with regards to someone I once considered a friend I don’t want to be so judgemental. Do I think I’m still under the gun from him? Yes. However I must restate how it’s important for rules of NO engagement. I still feel as if a final dramatic confrontation will remain a very stressful concept.

The sadness of living without sex

couple under garden arch surrounded with flowers

Found this BBC article from last year where some adult virgins as old as 61 to as young as 26. One guy just turn 40 in that article and finally found himself a girlfriend.

I hate to view living without sex as a sad condition. Just shows how we all desire to be wanted, but for some reason or another it just hasn’t happened. If it’s not sex it’s just love which is what I seek not just sex.

This article was yet inspired by an 60ish man who was a widower and had sex for the first time later in his life. What I can say for him is he at least experienced love & sex. Though I’m sorry to know that he’s a widower…

Oh and stay tuned, I got a post about love coming up hopefully next month. The month of Valentine’s day unless of course someone wants it out sooner! 😛

Is it Worth Being a Jerk?

I’ve been following this blog when I can and will share another post from here that seems pertinent to my blog.

Is it worth being a jerk? My experience has been I have no idea.

For yours truly being a jerk has often backfired. To be honest I could be considered grumpy and usually that’s around family. And beyond that it probably depends upon the job such as “The Show”. I would like to think of myself as a nice guy however I haven’t always acted like one, and yet I can be portrayed as “mean”.

I suppose the answer to me being a “jerk” is very uneven. As a nice guy people will cross my boundaries and as a jerk people can’t stand me. If the people I’ve run into are prone to making snap judgements, then they judge me really quick.

I suppose I have to decide to be a so called bad boy or a nice guy. I’d rather be a nice guy and I’d rather have a less conflicted life with very little drama.

I’d rather not have people I’m at odds with, and instead be around people who like being around me. However if you feel the need to stir conflict then that’s a problem. But then as I seek an available woman this is a challenge worth taking up.

The Functional Male

Do nice guys finish last? Are you better off being a jerk? Well, I’ve already answered this question in various articles to some capacity, but perhaps it would be useful to take a few minutes (or twenty) and isolate the topic. After all—to be honest, I sometimes find myself doubting . . . myself. I’ve usually gone by the philosophy that nice guys do win, but then, sometimes I’ll see something that makes me second guess myself. And then, after awhile of introspection, find myself only reaffirming what I already know. But let’s break it down.

The case for jerks

First of all, there absolutely is some truth to the idea that jerks, bad boys, alpha males, whatever you want to call them, do receive some advantages. Of course, the most obvious is that they appear interesting and confident to those around them. But there are other reasons too.


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Is a lady’s virginity more important than that of a man? Does virginity, whether for females or males a guarantee success in marriage? These and so many more questions arose after a seemingly controversial topic on the *Benefits of Virginity*.

via Male’s Virginity – Is it really necessary? — Simply Answers

Old stuff

I was looking for this. The website itself is no longer available, however, thanks to I can retrieve it. And the blog itself which inspired the post.

That blog Virgin at 50 has long been deleted, but it survives. Safe to say he probably was only writing it for two months and then pulled the plug. And who knows what ever happened to this Matt Savage character?

When I started this blog I was able to find this through a google search. Now not so much, perhaps his domain hosting has expired and he’s retired from doing relationship advice. Can’t find him anywhere on this internet!

As another aside I found this from this “How to lose your virginity” blog. A 38-year-old male virgin wants to know how to proceed with a married woman in a sexless marriage who is willing to help him lose his virginity. That’s a moral quandary I’d want to stay away from, I would never allow myself to be that desperate.


I have never seemed to have paid much attention to baselines. It’s unfortunate that people are measured by these standards.

For example you have to lose your virginity before you turn 21. You should get out here and date before you turn 40. You should graduate from college in four years. If you’re in your 30s and you don’t have children (for men & women) then the clock is ticking.

It’s on jobs also the older you get finding a good job gets more difficult. I had an aunt who worked intermittently in her youth, she had little issue quitting a job in a huff on the other hand I’ve never known her to hold a job. She got older and started looking and the opportunities for her got harder and harder to find. She often dotes on the accomplishments of her family more so than her own.

Anthony (the hustler) was one of those people who hit me with his own arbitrary baselines. He allows my personal life or any implications of it (for example no p*$$y and I’ve never directly discussed this with him) becomes the basis of his baseline. Or for one of the supervisors we know as “The Show” he sees her aging because she hates the job and thus as she ages and is getting less attractive to him “it’s over for her”. It’s like if his allegedly ravenous sexual appetite gets the better of him he wouldn’t choose her as a grandmother he’d share pics of as a conquest.

Anyway who cares about baselines? Who decides these baselines? They seem arbitrary and in fact probably created by many on the fly. It’s as if you’re expected to do x,y, & z by such and such point in your lives. For some of that I missed it, and yet doesn’t mean I won’t quite get there.

I can look at it this way until arriving at “The Hole” I never had a full-time job. In reality I never found regular employment until I turned 29 (at college bookstore which was temporary and later ‘The Show”) before that any work experience was temporary. I also didn’t finish college until I turned 29 as I said a while back it took me a while to finish at “Mission College”. While I accomplished some minor baselines of my own in my own time, I’m still not finished.

I just can’t let anyone else determine where I should be at this point. I’ll get to where I need to be in due time. The main thing I need not be is unhappy when I don’t meet anyone else’s baselines. Especially if their baselines benefit not me but only their own sensibilities.