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bigbear23ParticipantOctober 16, 2017 at 6:22 pm #152979
I like this girl for the past three years and as day passes by I think about her more and more. The girl that I like happens to be my best friends/business partners sister. About seven months ago I decided to tell him that I like his sisters and want to ask her out on a date and he told me he doesn’t have a problem with that. The only problem i have is I am not comfortable asking her out with the position I am in physically, financially and emotionally. I had told my friend a while back to not mention anything to his sister and he promised he wouldn’t. I am the type of person that likes to think deep and into details which hurts me at times. About three days ago my friend was talking to me and told me to ask his sister out on a date and told me to “trust him” and knowing me i started thinking more and more into details. So I am still not in the position that I want to be in life but my friend is telling me to sack up and do it and you never no it might work out. What y’all think?
F150ownerParticipantOctober 17, 2017 at 8:14 am #152991
I mean, what’s the worst that can happen, right? 3 years is a long time, you’re not complete strangers anymore, so there should be some trust built up at least.
candydudeParticipantOctober 18, 2017 at 11:48 am #153227
Hey bigbear23, your friend is your business partner. You trust him in matters of business, so you should trust him in personal matters, right? I know he told you that he wouldn’t mention anything to his sister, but I get the feeling that he did and she told him she likes you back. Life doesn’t have to be perfect for you to start dating. Who knows, maybe dating her will give you the motivation you need to get to where you want to be in life. So I think you should trust your friend/business partner and ask her out!
sasha.bellsParticipantOctober 24, 2017 at 4:24 pm #153897
All I can say is don’t miss your opportunity; give it a shot! Ask her!
timberman123ParticipantOctober 24, 2017 at 11:37 pm #153924
The worse that can happen is she’ll turn you around and the best that could happen is she actually says she likes you so it’s a win or neutral since you don’t really lose anything if she says no
TrumpetguyParticipantOctober 25, 2017 at 4:18 pm #154051
I used to pine away for months before finally asking who I was interested in out for a date. What I found was disappointing, I was being played as a back up guy if her current relationship didn’t work out, or I was only to be there for boosting their ego. Some times I would misread, but that’s rare. I stopped doing that a while ago, I cut to the chase sooner, and its almost relief to know she is not really interested or serious.
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