A
female
age
30-35,
anonymous
writes:Iv'e known this guy for almost 10 years now we have had on and off flings this entire time but nothing ever official and the boundaries have never been very clear. Well the past 6 months or so we have been hooking up...I've always wanted more with him...but here is the catch..He is my best friends brother and hes leaving for the military in a couple months. I want to tell him but im not quite sure how to approach it as we never seem to be in an ideal situation to have a private and serious conversation and its kind of a fragile situation since im so close with his family. How do I tell him or ask him what he wants?
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female
reader, Dorothy Dix  +, writes (8 December 2010):
Hi there. Perhaps one day soon, send him a text message asking if you can see him, because there's something you need to talk about privately, before he leaves for the military.
Don't say too much on the text message, and just keep it light and friendly so he doesn't get scared off too much.
Don't give any further details beyond asking if you can see him privately.
Then when you meet somewhere (by yourselves), you could just talk about how you enjoy being with him and the good times you have had together over the years.
You are also getting a bit closer now you say, so maybe you could ask him how long he will be away with the military for, and ask him if you could have a military address so you could write to him, while he's away. It's always lovely to receive mail when you're a long way from home. There's nothing quite like it really. It's even better than a phone call, because it's so very personal. A lot of thought always goes into letters, because they come right from the heart.
It's not a good idea to tell him how you feel about him or to ask him how he feels. The reason being, that it kind of puts him on the spot, and could be an awkward moment for him. So I don't recommend doing that at all.
In any case, by the way you are becoming closer, he can surely see how you feel by how well you both get along with each other. You would also have a pretty fair idea of how much he likes you -
(1) By how he talks to you.
(2) How he looks at you when you are talking to him.
(3) The places he takes you to.
(4) If he treats you with respect and caring.
There are so many telltale signs of how a person feels towards another. It's usually pretty clear.
Also in the last 10 years you have known each other, you have grown up to be adults, so things have obviously changed there a lot as well. You are now no longer children. So things are way different now, to what they were 10 years ago.
When you meet up with him - just the two of you - just keep it light and friendly, no pressure for a relationship. In fact, don't even mention the word "relationship", because it might make him uncomfortable. You want to enjoy your time together.
Just see how it goes, and gauge how he seems to be towards you as well.
In conversation, you could ask him about what he will be doing with the military and what his days will be like. This shows him that you are genuinely interested in him and in his life as well. It also tells him that you care.
Good luck and best wishes.
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