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Help!! Flirting with a friend/coworker/ex's friend

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Question - (6 September 2010) 1 Answers - (Newest, 19 October 2010)
A female United States age 36-40, anonymous writes:

This is gonna be long, i want to try my best to give both sides.

A year ago for about 8 months i was dating this guy that was all wrong for me, a total whore. I saw the best in him and tried to give him the benefit of the doubt at every turn. However, it got to the point were i was treating what we had like a relationship all while he was using me. I ultimately ended the relationship when I found out he had sex with numerous acquaintance of ours (one of whom had an STD). We have a lot of mutual friends that we are still close to. And now that a year has passed we are on friendly terms and I still wish him the best. We both recignize that we were never good together.

However, in March I began working with his best friend. Since then we've gotten to really know each other. We're good friends, we have a lot in common, hes one of the few males I'm genuinely comfortable around. We hang out in a group outside of work often and we see each other out even more often than that. Hes mentioned im one of the few women he's close to. Hes even said his friend is an asshole for the way things went. I always thought of our interactions as just being friendly until one day my boss pointed out that we flirt with each other like crazy!

Once she said it I began to notice him flirting with me, long hugs here, little touches there. We play the hit/poke game a lot. Ive always found him attractive and occasionaly wondered what would have happened if i had met him first. But I never pursued it because of his relationship with my ex and the fact that we work together. I always considered any flirting to be one sided if at all. I try not to flirt with him if i can help it. However, it's to the point where i hear from 3 different co-workers on a weekly basis that he and i should date or they ask if we already are. Ive met his father and even his dad said something to the same effect.

I find myself thinking about him a lot, however, hes an ex's friend and kind of roomate (my ex crashes there so often we joke that he should pay rent) as well as coworker. However, my boss loves the idea of the two of us dating and she knows everything that im writing here. Our friends tease us about our flirting (to our faces) and joke about our wedding.

He and I have never addressed it seriously and Im beginning to wonder if i should. Do I talk to him about our flirting and say it should stop, or address it to see where it could go? I would like to see where it goes, but I would hate to even possibly ruin their friendship. What do I do?

View related questions: best friend, co-worker, flirt, my boss, my ex, std, wedding

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A male reader, Ven United States +, writes (19 October 2010):

I see a couple of red flags before anything else:

1 - You both work together. As easy as it is to meet people in your place of employment, dating there leads to trouble. A bad relationship can hit you the wrong way emotionally and you ruin your job going through a break up. But you are a big girl, so I will let you decide how you want to go about that.

2 - It is my opinion that people who stay friends with D-Bags tend to be D-Bags themselves. In all the circles of friends I have ever had, a person who cheats multiple times gets more-or-less shunned for being that way. So I want you to ask yourself how well they get along now: if they are close, you should pass on the new guy. The fact that he lets the ex crash leads me to believe that he is not going to be that much better.

I definitely think you should talk to him and either get the flirting to stop or see where things go. I would tend to caution towards meeting guys outside of work who don't still accept your ex as a friend.

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