What would you think of a guy if his little sister tried to play matchmaker and convince you to go out with him?

I'm set to turn 30 soon, and while I've been on dates with a few different girls, and had a semi-serious relationship with a girl which didn't work out because of distance (she had to go back to the US), I've never even gotten to first base, never had a girlfriend. Understandably, I'm not happy about that, and never have been- I've always wanted a girlfriend, ever since I became a teenager, and still very much do. However, I want to find a girl, win her heart over and make her my lover myself. And my little sister (who's not so little any more- 2 and a bit years younger than me, 27yrs old now, and married for the past 6yrs, with 2 kids)?
What would you think of a guy if his little sister tried to play matchmaker and convince you to go out with him?
Yep. She never had any faith in my ability to do so on my own and to pick the right girl for myself, so she decided to take it upon herself, and she's now been doing this to me at every opportunity since I turned 18, more than 12yrs ago. She's tried to play matchmaker with me and at least 20 of her friends over the years; and still, even now, every time we're out in public and I spot a girl who I like the look of, she sees that I'm interested before I've even finished making up my mind whether I am or not yet, rushes over to them before I can, and sets about trying to chat them up and get their contact details on my behalf.

She hadn't tried to play matchmaker with me and any of her friends for the last couple of years though. Looking after her new baby girl, and moving a few hundred miles away with her husband and his family, meant that she didn't really have the spare time or effort. But my sister's gone back to university now, and she's at it again. This new girl who she's trying to match me up with now is admittedly different from the rest- she isn't a bible-basher, she's 21, and she seems like my type when it comes to her looks, personality and interests- but now my sister's probably already done the whole "Please, will you take care of my brother?" routine, what'll this girl think of me? Do I still have a chance?

Updates:
28d Bumping. Any help?

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What Girls Said 1

  • if i liked him yeah

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