Yes, this “inquiring mind” also would like to know. 
Inquiring Dopers, I’m back to update you. I’ve done it. It wasn’t exactly as I planned, went on too long, and was really sad. It ended up taking place over the phone in two conversations last night and tonight. He didn’t want to accept it. He kept trying to find a way to change my mind. He was in real denial at first and I really had to spell it out. I do feel bad for him but I feel relieved.
I did find out an interesting fact. Turns out I was his first. As in, I took his V-card. I did not know it at the time. I did know he was inexperienced, but didn’t know I had taken up with a real live 30-year-old virgin. He didn’t tell me at the time because he was embarrassed. I don’t hold it against him, but I don’t really know how to feel. It’s just surprising and I’m a bit taken aback.
I’m not sure what else to say right now. I’m just mulling it all over. Thank you again for all your help Dopers, I couldn’t have done it without you.
You did the right thing, Cymbeline.
Hard to do - and you will feel like shit for a while - but worth it in the end for both of you. It’s important that you remember that it was for him as much as for you, but keep reminding yourself of that.
Aside: strange that the figure ‘four months’ always seems to crop up in rebound situations. Has for me too, several times.
ETA: I’m 44 and I’ve never changed a diaper either. I don’t have kids of my own, and nobody’s ever asked me to help with their kid, thank goodness.
Thanks so much jjiim. Your words really do help. I’m just feeling guilty right now even though I know it’s the right thing. I know this hurt his already-fragile self-esteem.
Yeah the 4-month thing has happened to me a couple of times before too.
Good for you (and I think ultimately it will be good for him, too, even though I’m sure he doesn’t see that now).
The last time I had to do it it was horrible. We lived in different cities. She was so clingy and worryingly devoted to me. I knew that if I just turned up at her place spontaneously she would be overjoyed to see me and then I’d destroy her happiness, similarly if I told her I was coming to see her; but I also knew that if I told her I was coming to see her to talk about something she’d be in despair until I turned up to crush her dreams. So I decided to do it over the phone. Not the nicest thing, but better - and far more expedient - than the alternatives.
She hung up on me angrily, then a couple of hours later I got a flurry of hurt texts, having a go at me for not talking to her in person, and accusing me of seeing someone else (I wasn’t). I felt sooo guilty for weeks. And I did miss her occasionally, but not enough to do anything about.
And despite our collective hand-wringing, that sort of thing is just run-of-the-mill for dating. It would be easier not to be so empathetic, but that is the nature of not being a dick, I guess. Best thing you can do is distract yourself now, and not to dwell.
Well done. As for the V-card - I’m sure you may have changed how thigns happened if you’d known. But he didn’t give you that option by telling you beforehand, so don’t let it get into your head.
Soem particularly emo people might even lie about it to make you feel bad for breaking up, but given your description of him I think it’s probably true. So, good for him, he’s finally reaching the 17-year-old milestone of having his GF break up with him. Maybe you’ve helped him on the road to maturity!
Just don’t get sucked into repeated conversations with him. It’s over, and he has little to offer as a friend, so cut off communication ifyou haven’t already.
Thanks for updating us!
I think you did fine, and don’t worry about it being sad/taking too long. We can plan all we want (and we should at least try) but very few things in life ever go exactly how we planned.
Stick to the “relieved” feeling and take a deep breath and get some new hobbies or engage in the old ones. Good job. I almost never give out hugs on the Internet, but [hugs].
TruCelt’s words may sound harsh to you Green Cymbeline, but it doesn’t make it any less true. Your ex may deal with the break up by addressing the shortcomings in his life in the hopes of winning you back, or he may go from grudging acceptance to bitterness and spite toward you. However he handles your decision to end the relationship, you can’t be the one to shepherd him through the transition.
Kudos to you for making a hard but necessary – and ultimately kind – choice. Good luck.
Good for you! And fifthing, or tenthing, or whatever, the advice to make a clean break. And yeah, it’s natural to feel horribly guilty, but it’s the best thing for both of you.
Thank you jjimm. Yeah I felt at the time that it was best to do it on the phone when the subject came up, rather than pretend everything was OK on the phone and wait until I could see him face-to-face.
I am trying to figure out what to do to distract myself. Mainly I’ve been surfing the SDMB 
It’s a bit hard for me because I feel like I am going to be lonely for a while. Because he was the main person I hung out with, several days a week, for the past 4 months. I am going to make myself go out by myself this weekend to a concert. So that may help.
Regarding the V-card thing. I am trying to be an understanding person. But I have always wondered how it was possible to make it into your late 20s or 30s and still be a virgin? I just thought you must be seriously stunted to be in that situation. But here I was unknowingly dating a guy who was just that. Seriously, how do you make it to 30 as a virgin?! I feel a bit dirty, not knowing. I feel as if I was having sex with a 17-year-old, which is creepy. I just wish he had been honest. I had asked him questions about past sexual relationships, such as “how old were you when you lost your virginity?” and answered with a lie. In hindsight, it’s kind of funny to think of the effort he went into to illustrate the lie. :rolleyes:
I find it really strange if someone is a virgin at that age too, but you said he’d only been in one “relationship” before you, and that they never actually met, so it’s really not surprising. A lot of people only have sex in relationships.
If he didn’t want to tell you before though, I don’t know why he told you now.
Well he wasn’t very straightforward about his relationship past either. He alluded to some “several months-long” relationships in the past, before long-distance girl he never met, so I just assumed he was like any other normal person with a series of short relationships where sex was involved. I also assumed that he did the normal college dating thing. I guess I assumed wrong. But yeah essentially he has the dating history of an 18-year-old.
Dump him, “Tom” obviously isn’t the sort of person a woman would/should want to spend her life with.
It is considered impolite at this site to post in threads without reading them first.
Green, I want to repeat my advice of taking up a hobby or getting involved in something you have an interest in - it will both help stem the desire to run back to him due to boredom/loneliness and can be an opportunity to meet someone new who actually shares at least one interest with you.
Yes, and stop mulling over his virginity story. It sounds to me like you’re looking for an excuse to keep in contact with him. You either helped him or defiled him, and both or either of you sulking about it isn’t going to change a thing.
Find a new date. Do things. Email me your picture. Work out.
Woeg, I have lots of hobbies and am actually out right now at a concert, by myself, trying to get back in the game. No worries about lingering feelings cropping up, I have felt a huge sense of relief the past few days being rid of him.
Harry, I am not mulling over it, just a little sqicked out to be honest. I have a bit of a “uck” feeling. I’m annoyed he lied. I’m definitely not trying to stay in touch. Like I said, I am relieved. I am doing things and have already started looking for new possibilities.