What is the best way to approach telling my boyfriend it’s over?

Ok..Here's the dealio.

It's September 2008. A 19 year old girl with a screw loose is on a website named BeNaughty.com (like Match.com for the sexual thinkers). 2 weeks after joining and after talking to several people and meeting one (i'll call him Mark). I arranged to meet another one (i'll call him X-boy) 9 years my senior (believe me that's the smallest gap though). Anyway, time rolled round soon enough. It cost me £70 return to just barely be with him from Monday through to Wednesday. I don't crave attention 24/7 but i highly doubt an X-Box does either and that got 10 hours and 55 minutes a day, his bed got 6 hours, and the remainder of the 5 minutes was eating and me. I paid £70 that i could barely afford to see him (he lives 47 miles away), and he couldn't avoid the X-box and PS3 for 3 days.

Believing it to be a likely one off, i didn't give it much thought at the time.

I met up with a friend (Gipsy) i'd had feelings for in the November, but i had a realisation halfway through his intentions that i didn't want to change our friendship as i knew exactly what he was like with women. But somehow i felt guilty toward X-boy
An offer from a previous lover came by the next time X-boy wanted my company again. It was only out of a slight fear of the unknown i jilted Mark one day in December and declined his company to visit X-boy instead. Which, Mark was helluva lot cheaper, but hey ho. I spent my £70 day watching television, oh except for 5 minutes.

January was special, a birthday was to be celebrated and being that i was by then classed as his girlfriend. So i went, card and present in hand overnight. Except i had something on my mind. I was 2 weeks late for my period, it was 6 weeks since my last 5 minutes with him. I was all panicky. It was clear to see in my face, even my family wanted to know what was up. I was so scared cuz if i was pregnant, how would i tell him? How would he take it? So many thoughts were racing through my head. Oh and this is the day he actually wants to spend more time with me than the X-box, TV or PS3. I had protection but the "to hell with it" came and he said the words that struck my panic right in it's chords "well lets just hope nothing happens". If i could've left there and then i would've. But 13 miles from civilisation and a taxi rank, i made myself stay overnight. Hiding the tears within me.

That was my turning point that i knew this wasn't right for me. But i couldn't tell him. I left silently. Luckily i found out i wasn't baking buns in my oven. But his words had still hurt.

A few months on and his thoughts are in the place that if he had his own place i'd have moved in with him already. I wouldn't have. No matter how desperate i am to leave home, i wouldn't move in with someone i've been dating for 5 months and only seen 3 times. Shows how much he knows me.

In the meantime i had also made an agreement to meet up with another lover (Red) at a gig later in the year. I faced my fear and met up with Mark again and went on my travels and met up with the one i shall call DC. Having officially cheated on him with Mark and DC and partially with Gipsy i knew i was the wrong one. But friends and family have informed and hinted that he's not treating me the way i should be treated. That the relationship was entirely 1-sided from the off.

I've come to the conclusion that the only we'll know whether our relationship is built to last is if we end it, and we somehow from that meet in better situations or work more productively toward the relationship's faults so that next time we both know where we stand.

Problem lies in that i have never dumped anyone before. I've never tried to amicably end a relationship. I want to tell him how i feel, but i'm scared of how he'll take it. And the worst thing is that i can't afford to visit him to explain this to him; so i must do it by email or IM.

What do you think?

Can anyone help me in how i should go about it?

oh my word, what a palava!! to be honest it sounds like you have a few people to dump!! seriously though, after only seeing him 4 or 5 times and the way he treated you when you were there, he deserves no more than a text or a phone call and a serious goodbye!! just do it, you will never see him again if he is so far away anyway. in the meantime, stop trying to find men twice your age on dating websites, enjoy your youth and wait till you find someone really special that deserves you!!!

Tags: Dealio, Face, Fear Of The Unknown, feelings, Friendship, Gap, Girlfriend, Late Period, Match, Met, Old Girl, people, Ps3, Remainder, Screw, Something On My Mind, Thinkers, Watching Television, X Box