I have been dating this one guy for about two years now, off and on. When we first started dating, he chased after me and took me out to expensive dinners and such. In the beginning, I told him that I didn’t want a relationship and after that its all been downhill.

We do date other people but for some reason we always come back to each other and date off and on. He doesn’t call unless I call him first and then he starts the conversion about us hanging out and making plans. I haven’t talked about a relationship with him for a couple years now but I’m sick and tired of this off and on thing. We don’t break up or anything we just loose touch and then reconnect somehow.

His friends have made comments to my friends like “they are probably gonna end up together.” Does that seem like that he talks about me to his friends? What can I do to take this to another level? Should I just outright talk to the guy? I don’t want to scare him off. And if he says that he doesn’t know how he feels or ‘lets see where this goes,’ does that mean he isn’t interested? After two years a guy should know.. right?

Overall does it seem that the guy is interested in me?  Do you think it’s wrong to tell him that either something happens with us or that’s it and we need to go our separate ways?  I feel bad because I feel that I’m giving him an ultimatum.

Oh by the way, we haven’t slept together, so its not a booty call, I think!

See our guy’s response after the jump!

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Ask a Guy: Does the Guy I Work With Like Me? post image

There is a man I work with who’s behavior I can’t figure out. I didn’t realize it at first, but on several occasions he’s been staring at me when I’m out around the workplace.  When I’m in his vicinity in the cafeteria, I notice he dominates the conversation at his table. And  there have been a few occasions where he teased me a little bit.

What is the meaning of his behavior? Is he into me?

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A Guy’s Take on Female Fashion: Street Chic Edition post image

Sabrina sent me over some pics to review and give my straight guy opinion on “Street Chic Fashion.”

Street chic fashion, as I understand it, is when a girl spends tons of time and money on trying to look like she just threw something on without giving it any thought. Guys have their own version of this when we spend half an hour in front of a mirror trying to make our hair look like we have “bed head”.  Life is funny.

I’ve said it before: I am not a fashion writer and I have no desire to be. But I can look at a picture and give you my male opinion on it, and that’s just what I’m about to do…

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Ask A Guy: How Can I Help Him Get Over His Relationship Issues? post image

I’ve been seeing this guy for a few months now and I really like him. The thing is, he has some major relationship issues. All of his former girlfriends have cheated on him which has caused him to be very closed off and wary of relationships. I really think we have something real here but I don’t wanna waste my time with a guy who will always be too afraid to commit. Is there any way for me to help him with his issues and help him trust women again?

Read our guy’s response after the jump!

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Ask A Guy: Why Did He Cheat? post image

My boyfriend of over 3 years recently confessed that he cheated on me at a party one night with some girl he barely knew. He was incredibly sorry and felt awful about it (which is why he confessed) but said something just “took over” him and he couldn’t resist the girl. We’ve been having some problems lately, but we were working through them and we’ve had such a solid relationship up until now. I just don’t get why he did it. I mean he’s been faithful all these years, why now? And why this girl? And why tell me about it? Do I forgive him? I just have so many questions and don’t really know where to go from here.

See our guy’s response after the jump!

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Ask a Guy: How Do I Get Him to Marry Me? post image

I’ve been with my boyfriend for a while now. We’ve had our problems but have worked through it all and I really want him to pop the question already. There was a moment when he talked about us being married, but he joked that I should be the one to get him the ring.  The topic hasn’t come up again since and at this point, I am just about ready to give him an ultimatum- either he proposes or I’m leaving.  I’m also thinking of just getting him a ring at this point just to move this thing along!

Can you please help me figure this out?

See our guy’s response after the jump!

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Ask a Guy: Does He Like Me Or Am I Bugging Him? post image

I met a guy about two and a half weeks ago. We had a long conversation, he asked for my number and he texted me the next day. Since we met, I was never the one to call or text him first, I kinda always wait until he does. I don’t mean to ignore him because I do like him but I’m scared I might be bugging him.

Now, he really doesn’t text me as much as he used to (he always responds if I text him though). Do you think he might get tired of me or give up if I always wait for him to contact me? Should I reach out to him more often? How do I know if I’m bugging him?

See our guy’s response after the jump!

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Ask a Guy: Initiating Contact Without Creeping Him Out post image

So I know this guy in a band and we hit it off really well. I’ve only seen him twice and that was when he was on tour twice but we ended up talking forever. He’ remembered me both times and if you know guys in bands, you know they see so many chicks from touring all over America so its kind of hard to remember faces.

I just saw him three days ago and he was being pretty flirty and saying things like “what’s the oldest you have ever dated?” and “you have such a beautiful complexion.” (Btw, we’re only 5 years apart.) I wanted to text him in a couple months when he’s back home and off tour and ask him how he’s been and how the band is.

But there’s a twist- he never gave me his number. I got it from my brother because they’ve talked before. Do you think it would be weird or bad if I texted him? And do you think he’d be mad or happy to hear from me? I really need a guys opinion and point of view on this.

See our guy’s response after the jump!

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Ask a Guy: Should I Give This a Second Try? post image

Last spring break I started seeing my ex-boyfriend’s best friend as more than a friend.  It was unexpected… and we didn’t mean to become interested in each other. He had just broken up with his girlfriend and was hurt, but he was trying to get over her.

He gave me the option of either staying friends until he was over her or to keep talking. I decided that I wanted to keep talking to him because I thought it would help him forget about his ex-girlfriend.

Things were going well for about 2 months and then he suddenly wanted to take a break and said he needed space for a little bit. I understood, and in the meantime was hoping that he was OK and that things would soon go back to normal.

Soon after, his ex-girlfriend friend-requested me on Myspace.  I didn’t approve her, but I checked out her page out of curiosity.  She had added new pictures of her kissing the the guy I was seeing (the pictures were dated though).

I confronted him but he saw nothing wrong it.  He was turning things around on me and I just couldn’t handle it.  I stopped talking to him and a little while later she cheated on him again!  He learned his lesson and ever since then we’ve been friends, but haven’t started things up again.

I know that he truly cared about me and he tells me that he does. He wants me to be happy and wants for us to eventually give it another try to see if we still have the same strong chemistry that we once had.  Maybe I am crazy for asking this, but should I give him a second try?

See our guy’s response after the jump!

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