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How bad is my situation?

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Rookie Scribe
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I'm a white male in my early 40s, single, never married. I'm a bit on the thin side but in good shape (I have a 6-pack). I'm not particularly handsome; not ugly but maybe a little funny looking in the way someone like John Malkovich is funny looking. I'm certainly not cute. I'm pretty quiet and tend to keep to myself -- not outgoing at all. I'm intelligent (have Ph.D.) and successful (a millionaire, but you'd never know it because I live well below my means).

The caveat is that I haven't had sex or even been out on a date or kissed anyone in 20 years. I'm practically a virgin and have had sex only 3 times in my life. I don't mean three relationships; I mean three events, all awkward and, um... brief. I'm surely a lousy lay.

So, lets say you were the type of person who wouldn't mind dating a middle-aged man who was funny looking in the way John Malkovich is (or maybe closer to Nathan Barnatt). How big of a deal is the 20 year dry spell? It's a deal breaker isn't it? Is this the type of thing I should try to conceal?
Velvet-Voiced Titillator
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It shouldnt be a deal breaker, it probably feels like your the only one out there not doing it, but there will be loads of people feeling the same way you do.

It all depends on what your after, if your looking for some fun with no strings attached, if you never see the person again, it doesnt matter what your like, just take what you need out of it.

If your looking for something more long term, then the person you find should understand how you feel, and will take things slow.

You may think your funny looking, but there is someone out there for everyone, and it doesnt have to be about looks.

Hope this helps x
Active Ink Slinger
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i for one would not mind dating a successful, my aged, interesting looking man as long as there was an interesting person inside of there. and while i would ask why you chose not to have sex or be in a relationship for most of your life, it would not deter me. although id be afraid id hurt you ;)

heres an idea though..... you've done education, youve done successful career...now get out there and do some people! smile
littlemissbitch ~ professional face ripper offer, at your service..
The Linebacker
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First of all make sure your grooming is taken care of, hair, skin, teeth, breath. Maybe join some dating sites, clubs or social organizations for singles.

It is important to remember that not so attractive males can date and have a serious relationship with females much higher up the attractiveness scale. Since you are highly educated, stable and all, that plays highly in your favor. Many women your age have already had failed marriages and relationships with their one time great looking dream guy and want stability, honesty and integrity now in their relationship, a guy who doesn't cheat on them.

Mostly just work on talking to women, do not hover over them, stalk them, come on too strong and work on also not coming on too weak.

When you make it to the sex part just be honest. A lot of women would love to take charge and teach what they want and how they want it.
Alpha Blonde
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Honestly - I wouldn't mention your lack of experience until you're well into the relationship and you know she's already into you.

As is always the case for TMI (too much information), don't lead with this insecurity, don't confess it over dinner on the first or second or third date, and don't tell her before you have sex. It's not a deal breaker, but it might make her pause or reconsider or be weirded out.

Another thing to consider is - she might think you will have higher expectations of the relationship because of your lack of experience. Maybe she is looking for something casual and if that's the case, she will probably think sex will mean more to you than to her in terms of commitment and moving forward. You don't want to scare her off.

I'd just reserve that kind of tidbit for when you're settled into the relationship and have already had sex a few times... and that's "if" you choose to share it at all. Nobody really needs to bring up their past relationships or how much or what kind of sex they've had with other people. It's not really expected and it's very understandable to most people if their partner prefers to keep an 'air of mystery' on that one.

Just concentrate on who you are now and lead with more of a "I've dated but haven't found that something extraordinary yet" and the "I only want to get married once so I want to make sure it's the right person" type of thing for the reason why you're still single. Don't talk about sex. Keep the past a little mysterious as you're getting to know each other. Then once she's fallen for you, you can start getting into more complex conversational angles and sharing more of the past with each other.
Constant Gardener
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You are a millionaire - get some practice with some escorts to fuck you up til you are confident with your performance/game.

It costs lots extra for kissing practice.
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
Rookie Scribe
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Thanks for the input, folks. I appreciate it.
Active Ink Slinger
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As usual, DD is spot on. There is no need to volunteer all the information about your lack of experience. Just be cool about it, take things slow, keep yourself well groomed, play to your strength and dont try to be who your are not. And reasonably set your sights. Im sure you wil find some on who interested and find happieness.

BTW, I find John Malkovich kind of sexy in a weird sort of way!! HAHA
Active Ink Slinger
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I bet Nikki and I think similar being women of some experience...

If we did not know you were inexperienced, we would have a lot more fun!

Kisses!

Steph
Lurker
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Let's see now..you have a PhD and you're a millionaire..why are you here? There are plenty of outside venues where you could be looking or looked at. Spend a little cash to get a nice tailored wardrobe together; attend conferences in your field. Socialize. Be polite and learn how to make small talk. You'd be surprised at the results. That is all. Please return your tray to its upright position and debark at the gate.