Relationship Woes and Advice 22: In Which Two Problems Prevent Each Others' Solution

[dehro]

of course, be prepared to hug, smother and kiss random strangers if she should lean back and refuse contact...
no..seriously..don't it doesn't even work in fiction

[Sholos]

Hmm. Hopefully I'll be able to put that advice into action sometime. I did have her over for a movie night, but she didn't ever make any move to sit closer to me than she already was. We had a good time, though.

[dehro]

Hmm. Hopefully I'll be able to put that advice into action sometime. I did have her over for a movie night, but she didn't ever make any move to sit closer to me than she already was. We had a good time, though.

horror movies...last time I went to watch one with a female friend, she was all over me on account of being scared.
of course, if she's into them, she might not even flinch..in which case you can act all freaked out and be all over her

unless of course she is my sister..who is into them, but still freaks out and hides under her coat for most of the movie.

[Amiel]

We need a 'signs s/he's interested/likes you' post; I know that the signs themselves are legion and differ from person to person, but it'd good advice.

[noparlpf]

We need a 'signs s/he's interested/likes you' post; I know that the signs themselves are legion and differ from person to person, but it'd good advice.

That's a good idea.
I've figured out several girls were interested in me before they told me (I don't like rejecting people, I with they'd just stop), but I'm not really sure how.

[rogueboy]

So, I'd like some ideas. I'll spoiler it for the full backstory (long), but the basic question is this: if I asked someone out and she said no, with both of us saying that we didn't want the friendship to be harmed at all, and then I stopped interacting with that entire circle of friends (due primarily to stress and being busy with teaching, but could be seen differently), should I do anything in particular to show her that I've moved past that somewhat awkward interaction, or just treat it as if it never happened?

Details...

Spoiler

Show

When I started graduate school here, I ended up with a group of friends that I hung out with (6 of us total). Even split between guys and girls, and even split between in a relationship and not. Long story short, by the end of the first year, the other 2 guys had left the program, and our group was down to 4 (myself, N, M, and C), and M had begun a relationship. That left me and N as the only 2 not in a relationship, and me with a growing crush on her.

Fast forward a while, and I've spent a lot of time with this group (N in particular, since we work down the hall from each other). Main activities for the group is either game nights or going out to a bar if we need/want to get drinks, or to celebrate something.

Come this past January, I asked N out (by email, for various reasons that are closer to excuses than reasons, so I won't get into them). Delayed response, but she eventually replied, said no, and gave a couple reasons: religion is critical to her (I'm not religious, and lean towards the anti-religion side, which has come up in conversation with this group) and prior failed relationship (of hers) with a good friend being the ones I can remember. I responded to that saying that I appreciated the bluntness of her reply (she had commented on that in her email), accepted her decision, and that I also wanted to ensure our friendship stayed strong, as she is one of the better friends I have here.

Cue fate and poor timing, I get hit with a terrible student,* trying to get myself into crunch-mode on research so that I can avoid having to teach in the fall, trying to get back into regular physical activities, and general existing that took up pretty much all of my time. Overall effect: I stopped trying to generate any level of social interaction. If people invited me to do something, I joined, but otherwise, I just kind of drifted through things. Since all 4 of us in this circle are approaching a major presentation in our graduate careers this summer, all of us have been somewhat stressed (I'm assuming here, I haven't actually talked with anyone but C at all, really, and with C only briefly). Whatever the reason, none of us have organized any actual activities this calendar year.

I'm trying to re-establish this group as people I want to spend time with. First attempt was a game night last weekend, but out of 5 people I invited (N, C, and M, plus 2 others), 3 people couldn't make it, and I didn't hear from N or M (I'm giving them benefit of the doubt and assuming they just didn't see the email and aren't actively avoiding me). So I'm going to have to try to reschedule this, but I'm wondering if I should address (with N, specifically) the fact that there hasn't really been any communication between us since I asked her out? Or should I simply pretend that the whole 'me asking her out' thing never happened and continue on without bringing it up? Obviously, if she brings it up, we talk about it and the question is moot.

*Long story for another day: in short, she couldn't communicate in written form, and didn't accept that; went over my supervisor's head, got kicked back to my supervisor, then went over that person's head to get what she wanted - first student who's ever been able to actually make me angry while dealing with her.

Yay long post that isn't actually as long as I had been expecting!

Any input is appreciated.

[Lord Loss]

Signs She Likes You

The following list isn't very comprehensive, and it's specifically designed with signs women show when they're attracted to someone. A lot of it definitely applies to guys as well, but it's made up of personal experience and reading I've done, during both of which I've been looking for the female side of things, aiming to improve my luck with the ladies. So I don't really know many facts about male attraction.

1.Pupils dialated (enlarged)
2.Playing with hair (twirling, tugging, etc.)
3.Biting on or licking her lips
4.Chewing her nails.
5.Finds excuses to touch you, for example pokes you, pushes you, etc.
6.If you make accidental physical contact (lay your hand on hers, sit with your body pressed against hers), she doesn't pull away
7.When your eyes meet, she immediately shies away, or keeps eye contact for a few seconds, then looks away
8.You catch her glancing at you/checking you out
9.She mimicks your body language. For instance, if your arms are positioned a certain way, she may quickly do the same thing.
10.She laughs at all your jokes, even the really bad ones.
11.She looks at your lips while talk.
12.She glances downwards, subtly checking you out
13.Her feet and/or knees point in your direction while you're together, even if you're not standing/sitting directly near her.
14. Her arms are uncrossed. Crossed arms means she's uncomfortable around you and is setting a ''barrier'' between you.
15.Her head is turned slightly to the side while she's around you.
16.She playfully teases or insults you.
17.She asks questions, and gives long answers, trying to keep the conversation flowing.
18.She compliments you.
19.Her friends make suggestive remarks or imply that she's interested in you.
20.She gets jealous when you talk to or flirt with other girls.
21.If you're walking together and you slow down, she'll make sure to quickly catch up to you.
22. If you work or go to school together, she'll ''just happen to'' walk by places you're often found (cubicle, locker, etc.)
23.When she smiles at you, she smiles with a full set of teeth, not just the top ones.
24.She'll appear nervous. Scratching, glancing around, whatever it is she does when she's nervous she'll do when she's around you.
25.She'll do something that seems to indicate interest, then quickly act like she doesn't care, is ignoring you, etc. Women do this in order to appear uninterested.
26.She'll imply that she'd enjoy spending time with you, saying things like ''I'd love to see that movie'' after you say you'd like to see a movie or ''We should hang out sometime''. Things like that.
27.She'll inquire as to wether or not you're single, and who you're interested in/pursuing
28.She may rest her head on your shoulder.
29.Her palms are facing outwards/''pointing'' in your direction
30.Her shoulders are pointed towards you.
31.Her legs are wide/open
32.She leans while facing you, usually coupled with her shoulders pointed in your direction.

I'll try and expand on this later, this is just what I could think of off the top of my head. Feel free to criticize, give an opinion or contribute, I appreicate it. The information there isn't necessarily all right and it definitely doesn't encompass all the signs. Furthermore, just cause someone does (or doesn't) show one or many of those signs, it doesn't definitely mean they do (or don't) like you. These are just guidelines, and the only way you'll know for sure is by making a move.

[dehro]

mmmh.. in my experience, half those signs should be reclassified under "signs she might like you" and "signs she doesn't actively dislike you"
or the whole thing should be renamed "diary of a hopelessly optimistic guy"

[Pheehelm]

Signs a girl may like you:

She says yes when you ask her out.
She says yes when you ask her if she wants to be exclusive.
She says yes when you ask her to marry you.

None of these are one hundred percent guaranteed, of course, but for the most part they're pretty reliable.

[Objection]

Number 24 strikes me as a sign that she's creeped out by you, not that she likes you.

[Amiel]

Number 24 strikes me as a sign that she's creeped out by you, not that she likes you.

It has to be a good kind of nervousness (which is a little hard to explain and perhaps differentiate); if she likes you, she'll start fidgeting around you and becoming flustered. You'll know a good nervousness and a nervousness that arises from being creeped out.

[dehro]

It has to be a good kind of nervousness (which is a little hard to explain and perhaps differentiate); if she likes you, she'll start fidgeting around you and becoming flustered. You'll know a good nervousness and a nervousness that arises from being creeped out.

yah..the thing is,..if this is meant to be a list to help those people that are not emotionally (or experience-wise) equipped to recognize the signals of someone else..
meh..the entire list is open to plenty of misunderstandings and almost none of those signals has a single unmistakeable meaning..not even in the proposed context.

[Lord Loss]

Thanks for the feedback guys, upon rereading it it's pretty confusing and unhelpful to people who can't already tell these things... which sort of defeats the purpose. Any tips for revising it?

It's worth noting though that, if like a lot of those start cropping up (like 10+, let's say), it's generally a good indicator.

[Form]

Well, this is interesting. Sort of. I find myself desiring communication via PM to maintain confidentiality as much as possible.

PS: Not really for advice, more ranting I think.

[Dvil]

PM box open if necessary, etc etc

[Moonshadow]

Signs She Likes You -snip-

Signs She Likes You (Medium Rare)

1. She buys you "Tabasco" brand cologne.
2. When asked how/when she'd like to date, she replies 180C for 15 minutes.
3. You find your talcum powder replaced with salt and pepper.
4. She has this strange fascination with taking your temperature.
5. She uses cooking oil instead of suntan oil when you're at the beach.
6. There is a jumbo sized bag of stuffing mix in her pantry despite it being nowhere near Thanksgiving.
7. Pet names for you include "Hot stuff", "The other (color) meat" or "Sweet thing".
8. She insists that you get regular full body waxings.

[akma]

About signs she`s intrested: Showing that she likes your company and likes to spend time with you. Wanting as much contact with you (physical or social). Wanting to meet you alone. Compliments. All of this could also means she wants you as a friend. Women stratagy for getting a guy tends to be more about sending hints (in general), so pay attention.

I got a question of my own to add to the mix: How am I supposed to flirt?

[Glass Mouse]

Pheehelm and Moonshadow, thanks for the laughs


I remember a study concluding that women show very little difference in behaviour towards men they're interested in, and men they aren't. However, that started changing after ~10 minutes of interaction, where the interested women started to show a little more signs.
Someone in this thread linked to the study, I think?

[fergo]

So, I'd like some ideas. I'll spoiler it for the full backstory (long), but the basic question is this: if I asked someone out and she said no, with both of us saying that we didn't want the friendship to be harmed at all, and then I stopped interacting with that entire circle of friends (due primarily to stress and being busy with teaching, but could be seen differently), should I do anything in particular to show her that I've moved past that somewhat awkward interaction, or just treat it as if it never happened?

Details...

Spoiler

Show

When I started graduate school here, I ended up with a group of friends that I hung out with (6 of us total). Even split between guys and girls, and even split between in a relationship and not. Long story short, by the end of the first year, the other 2 guys had left the program, and our group was down to 4 (myself, N, M, and C), and M had begun a relationship. That left me and N as the only 2 not in a relationship, and me with a growing crush on her.

Fast forward a while, and I've spent a lot of time with this group (N in particular, since we work down the hall from each other). Main activities for the group is either game nights or going out to a bar if we need/want to get drinks, or to celebrate something.

Come this past January, I asked N out (by email, for various reasons that are closer to excuses than reasons, so I won't get into them). Delayed response, but she eventually replied, said no, and gave a couple reasons: religion is critical to her (I'm not religious, and lean towards the anti-religion side, which has come up in conversation with this group) and prior failed relationship (of hers) with a good friend being the ones I can remember. I responded to that saying that I appreciated the bluntness of her reply (she had commented on that in her email), accepted her decision, and that I also wanted to ensure our friendship stayed strong, as she is one of the better friends I have here.

Cue fate and poor timing, I get hit with a terrible student,* trying to get myself into crunch-mode on research so that I can avoid having to teach in the fall, trying to get back into regular physical activities, and general existing that took up pretty much all of my time. Overall effect: I stopped trying to generate any level of social interaction. If people invited me to do something, I joined, but otherwise, I just kind of drifted through things. Since all 4 of us in this circle are approaching a major presentation in our graduate careers this summer, all of us have been somewhat stressed (I'm assuming here, I haven't actually talked with anyone but C at all, really, and with C only briefly). Whatever the reason, none of us have organized any actual activities this calendar year.

I'm trying to re-establish this group as people I want to spend time with. First attempt was a game night last weekend, but out of 5 people I invited (N, C, and M, plus 2 others), 3 people couldn't make it, and I didn't hear from N or M (I'm giving them benefit of the doubt and assuming they just didn't see the email and aren't actively avoiding me). So I'm going to have to try to reschedule this, but I'm wondering if I should address (with N, specifically) the fact that there hasn't really been any communication between us since I asked her out? Or should I simply pretend that the whole 'me asking her out' thing never happened and continue on without bringing it up? Obviously, if she brings it up, we talk about it and the question is moot.

*Long story for another day: in short, she couldn't communicate in written form, and didn't accept that; went over my supervisor's head, got kicked back to my supervisor, then went over that person's head to get what she wanted - first student who's ever been able to actually make me angry while dealing with her.

Yay long post that isn't actually as long as I had been expecting!

Any input is appreciated.

The way I see it, if you agreed that your friendship shouldn't be harmed at all, then that means that you do [i]not[i] treat her differently to all your other friends. If you things have deteriorated between you so badly that you feel you need to bring up, then do so, but otherwise I'd hesitate. Especially as it seems you're having similar problems with some of your other friends, so dealing with her differently than you deal with everyone else should probably be avoided.

[rogueboy]

The way I see it, if you agreed that your friendship shouldn't be harmed at all, then that means that you do [i]not[i] treat her differently to all your other friends. If you things have deteriorated between you so badly that you feel you need to bring up, then do so, but otherwise I'd hesitate. Especially as it seems you're having similar problems with some of your other friends, so dealing with her differently than you deal with everyone else should probably be avoided.

Alright, that's about where I had come to on my own. Now I just need to figure out when I can make this stupid game night happen...

[Amiel]

Thanks for the all the signs, guys, it's excellent, especially Moonshadow's.


A bit of confusion at my end, recently met a girl - I'm friends with her friends; apologies if this is rather disjointed.

Spoiler

Show

Somewhat good
Whilst we were having dinner, I engaged her in a fistbump after something she said and I agreed with. Her fist lingered with my fist.
She maintained continuous eye contact for more than 5 seconds.
She exposed her palms to me, but wasn't looking at me.
We compared hand sizes in a circle, she voluntarily compared her hands with mine and rested her little finger against mine for a bit.

Not that good
She had a chance to sit next to me, but wouldn't. She sat diagonally from me. (This may have been because I had to sit diagonally from her at dinner - originally sat opposite her)
She engaged more in conversation with her friends there than me and wouldn't engage me in conversation that much.
She wouldn't single me out.
She exposed her palms to me, but wasn't looking at me.

[Moonshadow]

No problem. One must do one's level best to spread the occasional spurts of actually funny humour one has.

[dehro]

Thanks for the all the signs, guys, it's excellent, especially Moonshadow's.


A bit of confusion at my end, recently met a girl - I'm friends with her friends; apologies if this is rather disjointed.

Spoiler

Show

Somewhat good
Whilst we were having dinner, I engaged her in a fistbump after something she said and I agreed with. Her fist lingered with my fist.
She maintained continuous eye contact for more than 5 seconds.
She exposed her palms to me, but wasn't looking at me.
We compared hand sizes in a circle, she voluntarily compared her hands with mine and rested her little finger against mine for a bit.

Not that good
She had a chance to sit next to me, but wouldn't. She sat diagonally from me. (This may have been because I had to sit diagonally from her at dinner - originally sat opposite her)
She engaged more in conversation with her friends there than me and wouldn't engage me in conversation that much.
She wouldn't single me out.
She exposed her palms to me, but wasn't looking at me.

these signs mean pretty much nothing when listed aseptically over the net to people who weren't there and know neither of you two personally.
trying to interpret them for you is pointless because, as I said, we weren't there and don't know the circumstances behind each "sign"..
for you to try and interpret them rationally without being at least partially swayed by wishful thinking is equally difficult if not impossible.

sorry to burst any remaining bubbles..but without having a clear perception of the vibe underlying these gestures, the character and habits of the other person and the circumstances that bring these gestures about... it's really of no use to try and rationalise a single gesture, or a bunch of single gestures looking for a pattern and an indication of pleasure/displeasure in one another's company.
for all we know, her opinion about how close she wants to be with you might very well have changed over the course of the encounter.

also.. people seem to forget that at least as important as it is to try and understand the feelings behind these gestures, is to pay attention to the gestures you (generic you) are putting out there.. and to how the other person seems to interpret them or react to them.
the simple truth is that it's all a bit of a gamble if you don't have the clarity of perception to ..I'd almost say "divine" accurately the thought process or emotional process behind a gesture. and even then, only time will tell if your divination was correct.

let's just go through a couple of examples:
she sat diagonally from you. maybe she didn't want to give the wrong impression by sitting next to you (maybe this was not aimed at you but at a friend or something)..maybe she wanted a chance to observe you..something she might not have been able to do if she sat next to you and to that other person who would have requested her attention by engaging in conversation. (yes, her decision of where to sit might have had nothing to do with you..maybe the other person she'd have ended sitting next to had bad body odour)
she mantained continuous eye contact... or maybe she was just remembering something she'd forgotten to do and was looking in your general direction.. perception of eyecontact and it's relevance is often rooted in wishful thinking.
connecting and lingering fistbumps... seriously?
she wouldn't engage you in conversation... did you try to get one going and did she rebuke it, or did you just sit there waiting for her to come up with something to say? you may not be the only shy person there..

the above is just to show that "signs" need to be contextualized and even then, may have very little meaning at all..or one different than we would like them to have.

[Amiel]

Spoiler

Show

these signs mean pretty much nothing when listed aseptically over the net to people who weren't there and know neither of you two personally.
trying to interpret them for you is pointless because, as I said, we weren't there and don't know the circumstances behind each "sign"..
for you to try and interpret them rationally without being at least partially swayed by wishful thinking is equally difficult if not impossible.

sorry to burst any remaining bubbles..but without having a clear perception of the vibe underlying these gestures, the character and habits of the other person and the circumstances that bring these gestures about... it's really of no use to try and rationalise a single gesture, or a bunch of single gestures looking for a pattern and an indication of pleasure/displeasure in one another's company.
for all we know, her opinion about how close she wants to be with you might very well have changed over the course of the encounter.

also.. people seem to forget that at least as important as it is to try and understand the feelings behind these gestures, is to pay attention to the gestures you (generic you) are putting out there.. and to how the other person seems to interpret them or react to them.
the simple truth is that it's all a bit of a gamble if you don't have the clarity of perception to ..I'd almost say "divine" accurately the thought process or emotional process behind a gesture. and even then, only time will tell if your divination was correct.

let's just go through a couple of examples:
she sat diagonally from you. maybe she didn't want to give the wrong impression by sitting next to you (maybe this was not aimed at you but at a friend or something)..maybe she wanted a chance to observe you..something she might not have been able to do if she sat next to you and to that other person who would have requested her attention by engaging in conversation. (yes, her decision of where to sit might have had nothing to do with you..maybe the other person she'd have ended sitting next to had bad body odour)
she mantained continuous eye contact... or maybe she was just remembering something she'd forgotten to do and was looking in your general direction.. perception of eyecontact and it's relevance is often rooted in wishful thinking.
connecting and lingering fistbumps... seriously?
she wouldn't engage you in conversation... did you try to get one going and did she rebuke it, or did you just sit there waiting for her to come up with something to say? you may not be the only shy person there..

the above is just to show that "signs" need to be contextualized and even then, may have very little meaning at all..or one different than we would like them to have.

Your essay has served as a clarifier of intentions, and in the interest of furthering this discussion, I will form a framing context - I'm less remembering it as in the heat of the moment and swayed and more with rationality.

Throughout the night, she was repeatedly smiling at me and gave lots of prolonged eye contact and eye glances (there were some shy glances) - the instance of sustained eye contact was one where she also smiled (I should have clarified).

She was mostly waiting for me to start the conversation with her and then we'd have a sustained conversation with lots of tangents.

She engaged in teasing behaviour, with touching.

Fist bumps are pretty excellent; it isn't the fist bump but the connection and contact.

[Whip-poor-will]

Okay, Playground, I have a problem with a girl, but I really don't wanna post it for everyone to see, so if someone could send me a PM, that would rock.

[Anteros]

Signs a girl may like you:

She says yes when you ask her out.
She says yes when you ask her if she wants to be exclusive.
She says yes when you ask her to marry you.

None of these are one hundred percent guaranteed, of course, but for the most part they're pretty reliable.

I know this is kinda meant as a joke, but it's also good advice. The best way to know if someone likes you is to ask them. Now, I'm not saying to just completely ignore the flirting stage and immediately ask them if they like you...but at some point you have to "man up" and just ask.

[Whoracle]

As it happens, I need a place to vent, since I'm standing before a very hard decision today.

First, the setup:
- My significant other and me have been together for 4.5 years now.
- We've had our ups and downs, and the ups outweigh the downs by a fair margin.
- We had a long-distance relationship for half a year in the beginning, moved in together afterwards, lived together for 2.5 years, then due to my job I had to move and it was long distance again for another year.
- She planned on moving to me since mid-2011.

6 weeks prior to her moving to me, some things happened that led to me questioning if I was happy with her or just used to us being together, and I couldn't really tell. I needed her to come to me to be able to decide what the case was, mainly because over the course of our whole relationship I was away from my usual surroundings (friends, hobbies, etc.), and without her here I just couldn't come to a conclusion. I told her how I felt, and she ultimately decided to go through with the move, even with the risk of me ending the relationship.

She has been here for 5 weeks now. The first two weeks were filled with arguments and me feeling generally uneasy around her, since I was used to being alone for a year by then, but I decided not to make any hasty decisions, but rather to wait until things have settled a bit.

Now, three weeks later, I'm as positive as one can be that I don't want to be with her anymore. She's made friends with a couple of my folks fair enough, so she won't be all alone here.

Now, my problem is this:
We're currently living in a 1-room apartement. I'm prepared to move out for the time being, at least until she has a new place to live, or, if she wants to keep the apartement (unlikely, since it's not really up to her standards anyway), to look for a new one.

Should I tell her that the apartement is too cramped and one of us should rather look for a new place, and then, when one of us has the new place, end the relationship, so that she doesn't have to see me every day/get reminded of me every day due to my stuff still being around her, or do I end the relationship directly, thus putting the pressure of finding a new place on her in addition to the emotional strain of getting dumped?

What would you do?

Addendum: I like her. A lot. Just not in the couple sense anymore, so I want to hurt her as little as possible, whatever that entails for me, and right now I'm in physical pain over having to hurt her at all. Make of that what you will.

[Jukebox Hero]

Addendum: I like her. A lot. Just not in the couple sense anymore, so I want to hurt her as little as possible, whatever that entails for me, and right now I'm in physical pain over having to hurt her at all. Make of that what you will.

I've been in your shoes before, and sir, those are mighty hard shoes to stand in. But I find that it's like a band-aid. You gotta do it quickly, as soon as you're SURE that you don't want to be with them anymore (which you are). What I usually do is I lie and say something which I know will make them not want to be with me (there're constant rumors that say I'm gay, which are convenient at times like these). Sometimes, I say the truth. Depending on the type of girl you're dating, you should take a different approach. But if you act really sad and talk in a slow voice, you're more likely to hurt her. Speak clearly and frankly. Just say what you have to say and hope for the best.

Alright. So here's my problem. I was in a (mainly physical) relationship with a girl, let's call her Ellie (not her real name). We broke up pretty fast. I dumped her, and hooked her up with one of my friends. Neither of us were very heartbroken, and we still hung out after that. After she broke up with my friend, we picked up a more casual relationship (physical again). At the worst point, we were "hanging out" before she went on a date with her boyfriend. I started feeling really guilty, so I just cut off all connections with her, knowing that me+Ellie+alcohol = no self-control. I know for a fact that she is a nymphomaniac who takes advantage of people. She gets what she wants. Period.
Now, recently (I found out 3 days ago), she got into a relationship with another friend of mine (let's call him William). Now William is EXTREMELY emotionally unstable, and I'm trying to protect him here. He has little to no luck with women, and is constantly chasing them to no avail...
Unfortunately, I happen to be overseas, and will be overseas for a couple months. I need to break them up asap. I'm afraid that when it comes to the inevitable break-up, William might kill himself. I might be sticking my nose in other people's business, but I'm seriously worried here.

[dehro]

I know for a fact that she is a nymphomaniac who takes advantage of people.

and her phone number is....?


but no..seriously..there are limits to your responsability towards your friends. you should not try anything pre-emptive at least until you have factual confirmation that she is indeed doing stuff that will hurt him.
I've had enough female friends I "hung out with" regularily who then turned utterly straight/monogamous/loyal and boringly satisfied when the right guy turned up... stranger things have happened
as for your suicidal friend.. again.. there are limits to your responsabilities towards him.. you can't shield him from disappointments forever.
all you can do is talk to your girlfriend and ask her to be considerate towards your friend, take his emotional distress into consideration, and to let him down as easy as possible, should it ever come to that.
I don't see how you could do anything else without ending up really being the bad guy and doing more harm than good. playing god with other people's emotions is uncool whichever way you look at it.

[Jukebox Hero]

I realize that it is VERY uncool of me to do something like this, and usually, I wouldn't do anything like this. But...you see, Ellie has already dated 4 of my friends, and having exhausted one circle of friends of its relatively attractive members, has moved on to another...which just so happens to have me in it as well. I just need to remove the infection before it spreads.