My close friend of seven years has been dating someone for almost a year now. After some time being in a series of flings, this is his first attempt at a serious relationship and we (me and my other friends) do see everything going smoothly with his relationship (at least from the outside). This friend also travels a lot on work and returns back to town on weekends.

Over the last week, I have been seeing him online for hours on a hookup site every evening when he is in another city for work. I am single and I check that site often to just check things out. I ended up seeing him there online entirely by accident the first time, and I don’t think he has seen that I see him online.

My friend is 28, and has always been a little flirty by temperament, but I do not think he is the unfaithful type. He does get flirty in bars (even when he has been dating this girl) but it’s mild and mostly to get attention.

I could be over-interpreting, and he is perhaps only looking for a
harmless chat there. But I feel a little suspicious… especially since it is
very much a sex/hookup site. I don’t know if his girlfriend
knows/condones all this etc., etc. I don’t know if I should bring this up at all (since it is really none of my business and might somewhat hurt my relationship with my friend, because he does not at all like being confronted and is somewhat defensive by nature). But I feel bad for the girl if she doesn’t know. She is a nice girl and I feel it’s a little unfair if she thinks she is in a nice, committed relationship and he is cheating behind her back.

He has always been a very nice friend. As I said before, this is his
first attempt at a serious relationship and he has always been a little over-flirty in the past… so I wouldn’t be too surprised if he goes looking for sweets at the candy store. So, a part of me wants to just mind my business and not bother about it. Another part feels I should do something…

Nosy or Upright
If you’ve been friends with this guy for seven years, you should be able to say something to him without causing that much of a ruckus. If you’re afraid he’ll get defensive, could you possibly just mention that you saw him on the site while you were shopping there? Like “Hey, are you having any luck with that? ‘Cause I’m totally not†or something? That would at least get a conversation started. Then you could ask him if the girl knows he’s not exclusive or whatever. One of the important things about friendship is honesty, and if you tell him that you and your other friends are really happy to see him with this girl and that you are concerned that he might fuck it up, it might make him think twice about what he’s doing. Or, maybe he’ll tell you they’re not exclusive and it’s none of your business, in which case you can choose to either out him or drop the subject. Either way, if even mentioning it puts your friendship in jeopardy, then your friendship isn’t that great anyway.
During a study abroad program, I found a very good friend. We
both are shy, athletic and equally attractive. We both were nicely
welcomed by the girls in the trip; he as a mysterious guy, and I as a cute, harmless teddy bear. Since the program is filled with young and attractive people, both of us had been in dramas during the program. We can’t find girls who are compatible with us and still available. So, we have been both turning girls down and being turned down by the girls we talked to.
There is one girl that I started having an interest in. She is without a relationship. She has a nice personality and is quite pleasant. The problem is that, while I kept my interest quiet for now, my friend told me privately that he would ask this girl out.

I’m not sure if I should tell him that I am also interested in her, too. My attention to her has not developed into anything strong, and I value the friendship between me and this guy. However, I don’t want to miss a chance to talk to a girl that I find might work for me. Should I back out from this or what do I do?

Nice Friend
You should at least tell him that you are also interested in the girl. See how he responds, and then decide how to proceed. Obviously he has no claim over her, but you also don’t want to ruin your friendship, right? Well, what if she isn’t attracted to him but she likes you? Or vice versa? I think it is definitely worth at least a quick conversation with him. Clear the air and you will feel better.
I have recently started a new job. There is a policy regarding fraternization between people at different levels in the company. The thing is, I really like one of my superiors. We work in separate departments. I have no interest in him physically or romantically. I am very happy in my current relationship, and in fact I think he and my boyfriend would get along well. It’s just that there are not very many people at work that I can relate to, and he is one of them. Also, he is not from this state and has only been here a few months, so he doesn’t know a lot of people. Is it weird for me to ask him out on a strictly social basis? I don’t want to compromise either of us professionally.
New Girl
What exactly does the company policy say? And is this something that was made very clear to you when you were hired, or something that you understand from what other people have said? Unless you have been told that it is strictly forbidden for you to hang out with particular co-workers, I say you just talk to the guy. Make it very clear that you are not asking him on a date. Invite him out with you and your boyfriend. Don’t make a big deal out of it. If he tells you he can’t, then you have your answer. If he decides to join you, maybe you’ll make a new friend.
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