Interview with the Formerly Unfortunate Virgin

This week I feature a long and meaty chat (pun intended) with the gorgeous Tommy from The Formerly Unfortunate Virgin. I’ve been reading his blog for a while and I’ve always found it intriguing as well as funny. Read on to find out more about this puzzling young man.

Unfortunate virgin interview

(Note: They are really Tommy’s eyes)

Can you tell me your story in a nutshell? Why and when did you start the blog? How old were you then?

I was 28 and hadn’t been on a date since high school. It wasn’t all for a lack of trying, although my efforts were half-assed and inconsistent. With 30 approaching, being single and a virgin was starting to weigh on my mind. My friends and acquaintances were finding significant others, which reminded me that I too wanted to find someone. I was also starting to wonder why I hadn’t yet, especially when it seemed to come so easily to others. I found myself Googling terms like ‘28 year old virgin’ to find out how many others were in the same boat and why. Eventually I came across a female virgin blog and I was intrigued by her story. I thought I’d start my own blog just for shits and giggles. I didn’t really have much of a story to tell at the time, but I figured it might be fun to share my online dating travails. The rest is history, as they say. I never imagined that I would have the readership I have now, or that I would go on to meet some fellow bloggers in real life.

I’d be interested to know your views on how dating is different for sexually inexperienced people?

Dating is harder, obviously. There’s a lot more sexual tension for the sexually inexperienced person, a sense of ‘OMG is he/she going to be the one?’ If dates are hard to come by, then landing one brings the added pressure of ‘don’t screw things up!’ I’m definitely more relaxed than I used to be. Also: sexual inexperience typically goes hand in hand with general inexperience with the opposite sex.

When I finally started landing dates, having a conversation alone with a girl for 1-2 hours was a surreal experience. If you don’t have many female friends, something like that can take getting used to.

After so many years trying to meet romantic prospects, how do you maintain the interest and stamina to keep going? Do you take breaks, shake things up or what?

Sometimes I can’t maintain the stamina to keep going. Constant rejection is emotionally taxing. I did my best to keep my blog upbeat, but I spent collective hours offline whinging and venting to various blogging friends. I’m thankful they were willing to listen, but I’m sorry that they had to. A string of bad dates would leave me in a funk, and I’d have to take a break to regroup. Otherwise my funk would carry over and ensure more bad dates. So occasionally I’d take 3-6 months to focus on myself. I’d try new things, try to improve myself, and when I came back to dating I had a new perspective. I’d rewrite my profile for the hundredth time and swap in some new pictures. I’d also spend that time thinking about past dates and what went wrong and how I could improve future ones. Hindsight is a great teacher. But the interest is always there and that’s why I get back out there – that desire to be with someone. I’m happy with myself, but that doesn’t mean I always want to be alone.

What I enjoy most about your blog is the way you write honestly about your perspective as a man. A lot of your posts are also laugh-out-loud funny. I feel like, when it comes to dating, this is slightly rare – no BS, no machismo, just a frank dissection of what’s going on in your life, and often your confusion or uncertainty about what social signals mean. What sort of feedback do you get from readers – are they mostly men, women, virgins, who?

Thank you! I’m glad you enjoy them so much, that’s just the kind of fuel a writer needs. There is no BS or mystery with me; I’ll always give it straight. And if you like that sort of thing, then you should read The Rules Revisited. ( It’s good for any woman who’s dating and wants to understand the male mindset. There’s a lot to sift through and I haven’t read all of it, but most of what I did read left me standing on my computer chair applauding the screen. Undoubtedly it’ll rub some the wrong way, but that guy hits the nail on the head so many times and puts things way better than I could.

But I digress. I love keeping up on my stats, but never paid particular attention to how my readers break down.

I feel like I have more female than male readers, and mostly women that comment. There are a smattering of virgins who read and comment, but not as many as in the past.

Fellow virgins could relate to my story and felt better knowing they weren’t alone in their struggle. I’ve received some helpful advice, along with some weird or contradictory advice. I’ve had my share of trolls as well (they’re always fun). The best feedback was from readers I connected with outside of WordPress. I’ve emailed, texted, and even met some in person. JBlondie in particular got to know me pretty well.

How much of your post about the Craigslist ad genuinely describes you? None, some, all? Tell me about that social experiment, your motivations for it and the results?

Well… I don’t like kids, sports, video games, smoking, too-long shopping excursions, and people who run at the mouth like verbal diarrhoea. Maybe half of it describes me, and the other half is just balls-out crazy. As far as my motivations in writing it? When I’m awake late at night the carnival kicks in upstairs and inspiration strikes. I didn’t intend it as any kind of social experiment – rather it was purely for my own amusement. I ended up meeting three girls from that ad (which I hadn’t intended) and ironically I got along better with them than with most of the ones I met from my serious efforts on dating sites. Go figure. I wasn’t interested in dating any of them though, so we’re just friends.

In your post Chicks, you try an interesting social experiment and pose as a woman on a dating site. I love the way you reference historical precedents of this same idea, and your reaction at the results (about 250 visitors and 100 messages within 24 hours, then another 400 visitors and 80 messages during the first week). What did that experience show you about what online dating is like for (some young) women? And how does this compare with your experiences of what it’s like for men? Did it change your MO?

I thought it would be helpful to see what my competition was doing and how I stacked up. I already knew women got a lot of attention on dating sites, but that was an eye-opener. I didn’t think it would be as overwhelming as that. I was also envious. Most men have nowhere near the same wealth of options. It can be soul-crushing to send out 10, 20 or even 50 messages and only get one response. Most young women can post little more than a few pictures and are their inboxes are full.

But no wonder my own messages often went unread or unanswered. I was getting lost in the crowd and I needed to stand out.

I started trying a variety of openers. I paid more attention to what I wrote, composing at least several sentences and making sure to mention specific things from their profile. I’d often include a joke or something humorous if I could. Additionally, I figured out how to game the system through strategically timed profile edits, photo uploads, and match questions during periods of peak site activity. Only through a lot of effort was I able to maximize my matches and responses.

You say in one post that you seem to give off a ‘friendzone’ vibe to girls, and they don’t necessarily pick up on your interest. What do you make of that? In that same story you mention the possibility of you being on the autism spectrum (Aspergers). What’s your take on this now? At the time you mention that it ticks a lot of boxes and might explain much about your life.

That was another blogger’s observations (JBlondie). If she still had her blog I could link to the post she wrote about me. We met in real life and those were some of her observations. In fact I’d largely forgotten about them until you reminded me just now. I didn’t think I gave off a ‘friendzone’ vibe to girls, but apparently she did. I’m still not entirely sure how I might be doing so, or what to do about it if I am. Not to mention she had a boyfriend, so I wasn’t in a mind to flirt with her or treat her as anything but a friend anyway. As far as the Asperger’s thing, I did read up on it a little. Some of it sounded like me, and some of it didn’t. I haven’t given it much thought since then but… I guess anything’s possible?

I like the way you shine a light on dating profiles. Pretty much everyone hates writing them and most of us struggle with what to say and what not to say. In your story you detail what’s wrong with some women’s profiles you’ve encountered. I love your summary statements – here are just a few, but I thought your comments and observations were spot on, for both women and men who say these inane clichés:

  • “There’s a whole lot more to me but why spoil the mystery?” I don’t message people hoping they turn out to be interesting; I message interesting people.
  • “I hate filling these out. I don’t know what to say here – how do you sum up yourself in a couple paragraphs?” If you really can’t come up with anything to say about yourself, then I assume you’re a real bore and there’s nothing interesting to discover about you.
  • “Just message me if you want to know more.” Why do I have to make all the effort? What am I supposed to message you about when you don’t say anything about yourself? “Um… so what do you do for fun?”
  • “I’m just as happy getting dressed up and going out as I am spending the night in curled up on the couch in sweatpants watching a good movie.” If you actually have anything interesting or different to say about yourself, now is the time to do it. You’re not going to entice me if you sound like a thousand other girls’ profile.

And then you give a list of the worst-ever lines (these are also very common on guys’ profiles) eg –“I hate liars. I hate cheaters. I hate drama.”

You end by recommending to women that their profiles should be warm and inviting. Any examples? What’s your personal strategy after 5+ years doing online dating when it comes to responding to a profile that piques your interest?

Somebody suggested I do a similar post deconstructing men’s profiles in the same fashion, but I don’t think I’d have the fortitude. But what piques my interest are profiles that don’t read like a resume. Instead they contain specific, unique interests and have personality. If you’re a fun and goofy person, then you should have a fun and goofy profile. Plus it makes you more approachable.

For starters – don’t say it, show it: Don’t say “I’m really funny,” say “My current goals in life include visible ab muscles while not limiting my beer consumption,” or “Looking for someone I can do nothing and everything with. Preferably someone who’s sense of humor is as dark as my future.” Instead of saying “I like movies,” say “I have a fear of dating someone who doesn’t enjoy the movie Predator” or “On Friday nights I’m hanging out at The Mos Eisley Cantina, having a couple of drinks with some scoundrels.”

Those are actual examples from dating profiles I’ve read and liked. (Maybe I’ll even do a blog post with more examples.) Yet it amazes me how little effort many women make, saying ‘nobody reads these anyway’.

The problem with that kind of thinking is that there are guys who do, and you risk missing out on them because you gave them nothing to work with.

These are precisely the kinds of profiles I skip over myself, because for me it’s all about conversation starters. I’m not going to waste time scratching my head over what to message you when I can easily move on to a profile I can sink my teeth into.

In Tits you tell the story of getting hot and sexy with a girl but she keeps putting on the brakes. I like the way you describe the encounter from your (male) point of view. Can I just clarify how old you both were in this encounter, because it feels to me a lot like an early teens encounter, especially in her reluctance to get naked and explore sexual intimacy. What are your thoughts on this?

Funny you say that, because I only like reading about sexual encounters from the female point of view. Believe it or not Shorty was 29. There’s more to her that I detailed in a follow-up post I’m slightly embarrassed to admit that I overlooked her red flags and lack of physical attractiveness simply because I’d finally found someone interested in me. Rest assured I’ve matured and would never do that again. Shorty told me she had body issues on our first date. She told me she (might) take her shirt off for foreplay, but she didn’t like being naked during sex so she would put it back on. I didn’t really know what to say to that besides, “uh, okay…”. However, the one time we fooled around she seemed weirded out simply having her nipples exposed.

I like the lists you do (example below) – any ideas about the low second date follow-through? Am I right in reading those stats at that time to mean that you had 19 first dates but only one kiss? In another post you say, “In the meantime, I’ve been reflecting on how far I’ve come in just a short year. At 29 I was virtually dateless. Now I’m 30 with 30 dates under my belt…” How did you find your 30 dates and how did the stats go for you?

First dates: 19
Second dates: 2
Third dates: 1
Cancellations: 3
Stood up: 2
First kisses: 1
Sexual experiences: 0.6

If I remember correctly, that’s my lifetime counter. So at that point my only first kiss was from my high school girlfriend. After 19 OKC dates I still hadn’t kissed anyone else until I met Shorty. Also keep in mind that it was a steep learning curve dating at 28/29/30 after missing out on years of experience. It was another dozen dates after Shorty before I made out with anyone else, and in that case it was with a blog follower. In the end I went on three dozen OKC and Bumble/Tinder dates. 37th time was the charm, and that was with someone I met in the real world. My online dates got a little better as they went along, but meeting someone the old-fashioned way seemed to be the trick. I’ve been on another eight or nine dates in the two years since losing my virginity, only kissing one of those.

I would have liked more kisses and second dates, but… they kinda have to be interested in me in return.

Your post Swingers really leaves people guessing until the end. I found myself laughing and kind of hoping it might mean a change in luck for you. How much of this blog is about a love of writing and how much is about the topic or an outlet?

I’ve always fancied myself a writer. In fact I went to school for writing, but that fell by the wayside once music and dance became my new creative outlets. I still keep a daily journal (going strong since 1992!) and attempt the occasional short story. This one is my favorite. Over time my blog became as much about honing my writing as it was about honing my dating. I started including more stories like Dragon, which eventually blossomed into a second blog. I ended up taking that one down because it wasn’t getting the readership I’d hoped, plus a lot of it was really too personal to post. I still have all the material and may do something else with it someday. Every aspiring author talks of writing a book, and while I still might I tend to think blogging is better.

Books don’t give you the same global reach, instant feedback and reader interaction.

In your post Tango, you say, “I almost think that asking if a girl is interested is like asking a girl if she had an orgasm; if you have to ask, then the answer is no.” I get the feeling that reading women’s actions and body language is difficult for you to interpret. Any ideas on this, after all these years?

When I first arrived on the dating scene in my late 20s that was true, but I wouldn’t say it’s true now. Besides, their body language typically says, “I’m not interested,” so it’s pretty easy to decipher at this point. Teacher and Dancer Chick were only ones that really made me wonder. It’s still possible that Teacher was dropping hints, but in the end it didn’t seem like that was the case. It certainly wasn’t the case with Dancer Chick.

But overall I really don’t find women hard to figure out… apart from why they put up with so much shit from guys?

I feel like the majority of their dating problems are easily solvable by either A) speaking up or B) walking away. My joke that what you referenced applies to women as well. I see a lot of them over-analyzing or tying themselves into knots trying to figure out if a guy really likes them, wants anything serious, etc. Like, if you don’t know, then just ask him! And if you have to ask him, then aren’t you kinda answering your own question…?

In the comments section of that story, a reader disagrees with you. He says, “If women give hints, they want answers. Answers are direct; questions are open ended (or hints). Therefore… Be direct.” Have you tried to alter your dating behavior, and if so, what have been the results?

The comment just before that one told me that if I was “waiting for some obvious overt sign, it will never happen.” While on rare occasions it does happen, I don’t disagree. Nor do I disagree about needing to be more direct – something I’ve made an effort to do. But with the girls I’ve actually dated, I never had to wonder. I never had to show a screenshot of a text to a friend and ask him, “Do you think this chick likes me??” If she liked me, I could tell, I could sense it.

Is it possible that some women dropped hints and were more vague than usual about their interest, and I failed to pick up on it? Sure, but I doubt I missed anything over the years. I’m always on the lookout for the signs.

I also think we tend to project onto the opposite sex. It seems to me a lot of women think they have to read into men’s words and actions, when in reality men are much more direct.

Much in the same way that men would love to get pictures of women’s tits and vaginas, they assume women would love to get dick pics when in reality they don’t. At least that’s my theory.

I’m sure you’ve noticed from our chats on your comments sections how frustrating I find your luck with women. I just don’t get it at all – you seem to have a lot going for you but the most rotten luck. Women who are rude, bad mannered, only looking for ‘friendships’, sexually repressed or prudish, sexually disinterested or hung-up, women who string you along….what’s your take on all this? Are you just the unluckiest guy in New York or what?!

Sometimes I think I am the unluckiest guy in NY, although that’s an exaggeration. There are plenty of guys worse off than I am. And yes, some of the women I met were those things, but the majority I simply didn’t connect with. I find it frustrating too. I feel like I really do have a lot going for me and so much to offer the right person. In fact I’ve been thinking of writing a post highlighting my good qualities and why I think I’d be a great boyfriend.

I know I’ve expressed the comment to you before, wondering whether the responses you get on dates or via messaging is something to do with your locale? Do you think it’s a New York thing or what’s your theory? I said that in my view, Australians are generally friendlier and more easy going than Americans and your experiences seem to bear that out.

Australians may be friendlier indeed, but there are plenty of people dating successfully here in NY so it can’t be that. Going by the blogs I read, people are going on shitty online dates all over the world. I think that says more about online dating than it does about my location. Nonetheless I’m sure there’s still stuff I can improve on so I’ll have better luck out there.

A lot of your stories, like Crazy seem almost too bizarre to be true! Perhaps you have a knack for attracting very, very strange people? That story made me laugh so much I had to explain myself to my son!

Well, I’m a very, very strange person, so you’re probably right. The problem is that they’re not the right kind of strange. Everyone is crazy, I just need to find my compatible crazy. But that story was nothing. You would have liked my other blog where I compiled all my crazy Dad stories. Those really took the cake.

I’ve described your blog as funny (hilarious in places), articulate and perplexing. Sometimes it seems to me a living example of the idea that men are from Mars and women from Venus! Your ideas about women and sex (and experiences with so many prudish women) really surprise me. What have you learned from the time you’ve spent reading blogs by women about sexuality and relationships?

I was surprised to discover that they were more sexual than I ever thought. Before that I always had the impression that guys were insatiable horndogs and women were the reluctant gatekeepers of sex. I was even more surprised to learn the inverse is true sometimes.

You mean women can have libidos surpassing men’s? You mean women can be the initiator, the aggressor in the bedroom? You mean women can be into kinky stuff?

Sadly I’ve yet to discover these things first hand, but it’s nice to know that they’re out there… somewhere… But I still feel like those are the exceptions rather than the norm. I suspect if you polled a large group of men, many of them would have experiences and beliefs in line with my own.

I liked your story about your first sexual experience (aka intercourse) because it was, frankly, refreshing for me to read an account from a guy. If you could give a message to every virgin out there who wants to change that status, what would it be?

For one thing, don’t visit an escort unless as an absolute last resort, as some advised me to do. If you’re a virgin due to lack of confidence or other issues, visiting an escort won’t solve that and could even make things worse. The last thing you need is to compound those problems with even more negative associations about how you lost your virginity. ‘Just be yourself’ is kinda lousy advice too. I’d wager that most virgins are being themselves. Doing more of the same won’t work. And I don’t mean trying to be someone you’re not. Instead, work on being the best version of yourself. Take a step back and try to look at yourself objectively. Ask, ‘would I date me?’

If you feel there are things holding you back from dating, tackle them head on. Cultivate your skills and hobbies and social circle. Live as close to as full a life as possible, and then things will fall into place. It may take time, but once I found that sweet spot, things happened for me.

And finally, I made this comment on the blog of another self-identified virgin male – I’d like your opinion on this:

“I’d like to suggest that we re-frame this whole virginity thing. Surely your satisfaction with living your life as a human should be based on your feelings of intimacy with other people, amongst other things. Not one fairly meaningless act that looks at sexuality from a patriarchal perspective of conquering and ‘spearing’ your woman. I politely suggest that it’s time to reframe virginity as a political statement about selfhood. Altering that statement/experience/identity should be based on the health/success of a relationship in your life that warrants change – in this case, exploration of sexuality. This is a huge spectrum, as I’m sure you know, of sexual behaviours that may or may not include penetration of ‘a body part’ by a penis. The notion of deflowering really is very out of date.”

I agree!

39 thoughts on “Interview with the Formerly Unfortunate Virgin

      1. That’s fab! The way it works is that you send me your email via my contact form, then I devour your blog for interesting angles and stories, then I send you a list of questions that you then answer at your leisure. I have a couple in the queue so I’ll start reading the backstory of your blog now 🙂

        Liked by 2 people

  1. This is another world to me. I probably started early. Drinking etc… from 14 on sort of fixed all the knots.
    Being part nerd inside though I always found other minds interesting and was usually kind, even sometimes protective, of other guys who were underdogs. The only ones I did hack on were those who were predatory of girls at sister schools then bitched in packs about people they pretended to like but in actual fact hated. I have always liked and respected other guys who love their partners even if only a one night stand.
    Maybe it has a bit to do with upbringing from one or both parents.

    Liked by 1 person

  2. Thanks UTC for conducting such an incisive interview. Thanks T(F)UV for your characteristic candor/humor/decency/… I could go on and on with the /… business but – for Tommy’s sake – I shan’t. A thoroughly enjoyable read!

    Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s