What’s up, doc?

I’m a regular reader of your column, and while we may not agree on everything, I value the genuine empathy you have for your audience and thank you for taking my message.

I’m a 26 year old virgin for a number of reasons: a conservative upbringing, delayed interest in the opposite sex, body image issues to name a few. Despite my issues with women, I have strong relationships with my family, several close friends, and a fascinating job on Wall Street where I feel highly valued by my superiors and colleagues.

While I initially started college far from home and generally had the “traditional college experience” my freshman year, after a year, complications relating to homesickness, an ill (but long since recovered) relative and some financial concerns resulted in me transferring to a state university where I commuted from home and worked about 30 hours a week on top of that. I didn’t get socially involved at my new school, aside from a couple networking clubs relating to my major/career path.

Since graduating college, I’ve dealt with the same increased isolation typical of most people my age. Work keeps me fairly busy (typically 50-60 hours per week in addition to my commute back home) and my friends have largely scattered across the country and around the world. I’m by no means unique in this regard.

About two years ago, I met a young woman (let’s call her Peach) through a video game discussion forum and we initially formed a casual virtual friendship through Twitter and Snapchat. Our chats were platonic at first, about common interests including gaming, music and politics; over time, she virtually introduced me to one of her close IRL friends (let’s call her Zelda) and I started talking to both of them. While I find both of them attractive and intelligent, I know they live on the other side of the country, so nothing would realistically happen with either. Not to mention, both are about 4 years younger than me.

A little over a year ago, I was home alone late on a Friday night when I messaged Zelda randomly. In our conversation, she complained about the struggle of being a broke college student during the holiday season, when I got the nefarious idea that maybe I could help her out. I don’t think she expected me to proposition her that way, but I offered her money to sext and trade pictures with me and she agreed. I figured that word would get out to Peach sooner rather than later, so I ended up making her the same offer.

Since then, in addition to our regular conversations, I typically sext with both of them (individually) about once a month, and while it’s surely not money I can’t afford to lose, I’ve spent several hundred dollars on this over the past year.

I’m not under any delusions that anything would come out of this other than me blowing off steam. Both of them ask me for advice about guys, and I know that they’re both actively dating and hooking up (albeit with some social awkwardness) at their respective colleges. They’ve been up front with me that they’re in this primarily for the financial incentive. They’ve told me there would be no hard feelings if I was to stop, although I would probably begin to break contact with them in order to move forward.

I know within my heart that I need to stop this, that it goes against the values I wish to have, and I feel guilty as hell for even starting. I feel entitled and exploitative; moreover, I’m afraid that if I should ever find myself become an A-list name for any reason, even with my current track record, I’m on the fast track to being #MeTooed. Further, since we all know one another’s names and whatever details we share via Twitter, it’s possible that either of them (if they were so inclined) could hold this over my head.

At the same time, I attribute my inexperience as a contributing factor to this. While I know I shouldn’t feel this way and that it’s antiquated, like most adult virgins, I realize I subconsciously feel like less of a man until I prove that I can attract a woman. Although I don’t generally feel lonely in my regular life – I keep myself busy with work, friends, the gym, movies, volunteering and the like – I couldn’t shake the late night romantic loneliness and horniness, so I kept going back to the well in order to somewhat try and fill the void.

It’s recently dawned on me that Peach and Zelda probably think I’m pathetic or laugh at me behind my back, and I’m quickly finding myself able to divorce the fantasies from the reality of my situation. More importantly, I’m afraid that they only agreed to do this because I made them nervous, uncomfortable, etc and somehow creep them out. I would rather not make any woman scared in my presence going forward.

This finally brings me to my question: assuming I’m able to break this habit and not relapse or try it again with another woman, how do I move forward? Can I really just move on with my life and pretend this never happened with women I meet in the future? If I confess this to someone I date in the future, I assume she’d take off running, that I’d be branded a pathetic creep, or worse yet, predatory. I’m afraid to even bring this up with friends or parents, let alone someone I know less intimately.

When I brought this up with Peach and Zelda, they suggested I forgive myself and just learn from it which doesn’t help me much from a tangible standpoint. I’ve considered volunteering with a women’s shelter or the like in the future, but I feel people would assume I’m there for the wrong reasons.

I realize I’m rambling here, but my ultimate question is how do I repent? Do I even deserve another shot at dating? If so, how long should I wait?

Thanks for all you do,
New Decade, New Me

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