This is kind of involved...

Background first:
I have been seeing this guy for 5 months or so. Let me start with the fact that he is 26 and has not had a serious girlfriend EVER. He is extremely good looking, but he is not very flashy, although he can be a flirt. I don't think he is gay - just very hesitant to open up. When we first started dating, he was more into me than I was into him (I had just ended a 4-year relationship, so transitioning was hard). In fact, at the beginning we took a break for 3 weeks because I told him I needed to sort things out. When we got back together, he told me he was really happy about it. Then, I started to like him more and being myself more... I can be sort of blunt at times... plus we slept together... a month after this started I asked him how he was feeling about "us"... and he told me he was not sure if he liked me as much as before. Wow, that hurt! After a few more episodes like that, we agreed to try to be just friends for the time being -- I suggested it and he said "Maybe that's best for now." According to his roommate, he never was dating anyone else but me, so I don't think it was another girl. When we would hang out "as friends" there was always this tension... he would be hot and cold... so I stopped talking to him, and then he started coming around again, but I continued to blow him off for 3 weeks. Anyway, I saw him at a mutual friend's 30th birthday party a couple weeks ago. I hate to admit it, but I drank too much wine, and we ended up sleeping together. According to our friend, he was happy that we are "back on". He has been emailing me this week but we never discuss his feelings -- I am way too scared to go there now. It's just I am very insecure around him after the things he said... I feel like he could change his mind at any time... he told me his relationships only last a couple months usually... I just really like this guy and I would like to see if something more could come from this, but I freak out if he does not respond to my emails. He is very hard to read!

The situation: So yesterday he sent me an email with a joke in it... I responded... we emailed back and forth a bit... he told me a story about his friend... I sent him a picture I found that I thought was funny, but I am wondering if he was offended, because no response. My cousin told me not to freak out, but I can't help it after what has happened with him... feel like I messed up again... we are supposed to hang out tonight... how do I calm down?? Ugh, I feel so insecure!!

Applehead, I really feel your frustration. I'm also in the same situation as you, dating a guy that is going hot and cold, also for about 5 months!! And who has never had a serious relationship ever! I'm trying to understand him too. These guys are just so hard to read!! I'm at a point where I'm seriously considering stop seeing him. The question that keeps running in my head: should I be more patient and be more understanding, perhaps he's scared of opening up and scared of getting hurt? But at the meantime I try to not put my eggs in one basket? (meaning date other people while still dating him). Or stop this first, and then try opening up my heart to others? Sigh. Difficult decision.

Wow a lot of info there. Not sure what I'd advise. But I should caution you that guys are pretty consistent, even in their flakiness. The guy he appears to be after 5 months of dating should be starting to be close to the picture of the guy he'll be for you from now on.

That may not be comforting.

There's an old joke/adage I wish more people would take to heart:

Men and women go into relationships with completely opposite expectations and results.

Men marry a girl he likes just the way she is and hopes she'll never change...but she does
Women marry a guy knowing he will change someday...but he doesn'tFunny, but stereotypically correct mostly. Keep that in mind. IN the 6-12 month mark, the guy you see may be pretty close the guy he'll be. Think about it.

this is kind of involved....

Background first:
I have been seeing this guy for 5 months or so. Let me start off with the fact that he is 26 and has not had a serious girlfriend EVER. He is extremely good looking, but he is not very flashy, although he can be a flirt. I don't think he is gay - just very hesitant to open up. When we first started dating, he was more into me than I was into him (I had just ended a 4-year relationship, so transitioning was hard). In fact, at the beginning we took a break for 3 weeks because I told him I needed to sort things out. When we got back together, he told me he was really happy about it. Then, I started to like him more and being myself more...I can be sort of blunt at times...plus we slept together...a month after this started I asked him how he was feeling about "us"...and he told me he was not sure if he liked me as much as before. Wow, that hurt! After a few more episodes like that, we agreed to try to be just friends for the time being -- I suggested it and he said "Maybe that's best for now." According to his roommate, he never was dating anyone else but me, so I don't think it was another girl. When we would hang out "as friends" there was always this tension...he would be hot and cold...so I stopped talking to him, and then he started coming around again, but I continued to blow him off for 3 weeks. Anyway, I saw him at a mutual friend's 30th birthday party a couple weeks ago. I hate to admit it, but I drank too much wine, and we ended up sleeping together. According to our friend, he was happy that we are "back on". He has been emailing me this week but we never discuss his feelings -- I am way too scared to go there now. It's just I am very insecure around him after the things he said...I feel like he could change his mind at any time...he told me his relationships only last a couple months usually...I just really like this guy and I would like to see if something more could come from this, but I freak out if he does not respond to my emails. He is very hard to read!

The situation: So yesterday he sent me an email with a joke in it...i responded...we emailed back and forth a bit...he told me a story about his friend...i sent him a picture i found that I thought was funny, but I am wondering if he was offended, because no response. My cousin told me not to freak out, but I can't help it after what has happened with him...feel like I messed up again...we are supposed to hang out tonight...how do i calm down??? ugh, i feel so insecure!!!


There's a really good book called 'Why Men lie, and Women Cry' you might enjoy. You are trying too hard, reading too much, men don't think like us. Enjoy the friendship, enjoy the sex, enjoy the good times - don't keep asking him how he feels. He wants you to know - he'll tell you when he's ready. He's not had a steady relationship, is probably unsure - especially if you're looking 'where this might lead'. He's worried that he wants it easy at its own speed - feels like you are putting pressure on him, that's why he's blowing hot and cold. Insecure women come across as 'clingy' - men don't like that. My 19yr-old daughter has a policy that if a man says he'll call and he doesn't, when he's said he would - she simply goes out with her friends and won't wait. If he calls and expects her to fit in with his plans after that - she makes him wait to fit in with hers. It works.