The trouble with the go-between

Dear The Turquoise Bag,

I've had a read through your blog and thought it would be fitting to write you on my little dilemma. I have a good friend of mine who confided in me about a woman that he liked and as any good friend I encouraged him to pursue her. He is very shy and so I took matters into my own hands in order to befriend this woman so as to introduce her to my friend. As luck would have it she befriended me and I introduced her to my friend but unfortunately she started to show signs that she was interested in me. This I only noticed once I had introduced them and withdrawn from the scene. I was prepared to talk to her but my friend said that he could never face her if I revealed the whole story and to leave it to him to explain. As it would be my friend never did and after only a few attempts at trying to pursue her, he seemed to give up. It has been several years and my friend has since said he is no longer interested in her.

Now my reason for this story is to put you into perspective of where I am currently. I happened to run into this aforementioned woman by chance at a coffee shop and I sat down to catch up with her. There was an awkwardness to the conversation which I believe may very well have to do with where we left off previously. We are both unattached so that is not an issue but we both have come out of serious relationships and I'm not sure if we are experiencing a “rebound” moment or if it has to do with what happened several years ago. I must admit that I have thought about it and I am not against the idea of us dating but I am concerned that it might be unwise considering our past and current states. I have met with her a couple of times now and I have a feeling that she may still wonder if something could happen between us and admittedly so do I. I believe that it may be an opportunity I will regret not taking if I past it by based on complications.

My question is, if you were this woman would you appreciate it if I explained to you why I did not make a move previously or would it be more appropriate to ask her out on a date and if she does bring up the subject to then say that I messed up? I'm still friends with the man who liked her and I wouldn't want to blacken his name or sound like I'm coming up with an excuse. As you can see I am in a bit of a spot and would appreciate a well informed woman's perspective.

Yours Sincerely,
Leonard

Dear Leonard

Thank you for reading my blog and for writing to me. Wow, what a story. So she’s the one that got away…from your friend? Mmm. Yes, it’s always complicated when friends are involved. I see that your question is ultimately whether you can spill the beans and tell this lovely lady about what had happened in the past? Although I have a feeling that you are actually asking a number of other questions. Actually, not a feeling, I can see that you are asking a number of questions and so I will certainly give you a woman’s perspective but I am going to make a few other comments on your situation.

Firstly, I think you are trying to decide if you’re going to defy the “the bro code” by getting involved with this girl. I am not really sure, since I am not a “bro”. It seems that you really care about your mate and don’t want his feelings to be hurt and that’s why you didn’t reveal (all those years ago) why you did not pursue the lady in question, out of respect for him. Well done! Bro’s before ho’s… That’s what I always say. Ok. Just kidding. (Eek. I’m probably going to get some hate mail from the feminists for writing that. Please forgive me – this is a humorous column as well and we handbags can’t take ourselves too seriously!) On a more serious note, I do think you have to consider your friend and be totally honest with him should you decide to ask her on a date. Since you say he’s not keen on her anymore, you probably out of the woods but best to come clean anyway. You would not want a friendship to sour over a relationship that might not even occur!

Ok, with that out of that way we can move onto the rebound issue. So, you just came out of a relationship, hey? Let me ask you one question: are you bored and need of some excitement? If the answer is yes, then don’t even think of asking her on a date. You’re wasting your time and hers. You need to get over the junk that happened in your last relationship and once you’re in the position where you have met someone and from the little you know of them, they seem like someone you could fall in love with and spend the rest of your life with, then only are you ready to start dating. But if this is just a notion of, “I’m bored, lonely and in need of companionship” – get yourself a dog. Any dating done for selfish reasons is doomed for failure... (This is the advice I would give the woman in question too, by the way.)

Now assuming you (and she) are in the right frame of mind to be in a relationship and you could genuinely see yourself in a forever type of relationship with her (the only one worth having) then I would have this to say about your question: let sleeping dogs lie. Don’t bring up all the stuff about your mate liking her and you acting (in good faith) as his agent in this scenario. Rather leave it until she brings it up – that is if she ever brings it up. Sometimes when we know of weird vibes that went down with someone of the opposite sex, we become overly aware of them and may see an awkwardness that does not exist. (I am not saying there isn’t awkwardness – just that you may be imagining it.) You may meet up for a date or 2, only to find there is no connection and then to go into all that history for nothing…

My rule of thumb is to always be honest but only on a “need to know” basis. She doesn’t need to know at this point why you didn’t pursue her all those years ago. Should you start seeing each other for real, I would then come clean in a matter of fact way – not making a big deal about it. I think it’s one of those things that you could have a chuckle about in the future? Not at the expense of your friend! When you do tell her (although I am sure is she has an EQ she will have figured out your mate liked her) do it in such a way that your friend is honoured in the conversation. Keep things simple in the beginning and if you have a lasting chemistry then your friend’s interest in her will not matter – probably just flatter her and make her think more highly of you for honouring him. I think a lesson that can be learned from this is to never act as the go-between in your friends’ love life pursuits. 9 out 10 times the girl thinks that go-between likes her. It creates massive headaches…

All the best and let me know how it goes. I enjoyed this question and am pleased that you’re thinking about women’s perceptions in these dilemma’s of life.

Yours sincerely
TTB