A
male
age
51-59,
anonymous
writes:Ok I need some thoughts on this, I have met a younger girl through my work, I own a small maintenance company and have met with her a good few times to discuss various repairs she needed in her home, she is attractive and around 25, I do know she has 2 year old but is now single. I do find myself flirting with her there is something sweet about her, she always seems to respond with cute wee smiles. I want to ask her out for dinner and make it clear that I am attracted to her. But i am in my 40s and don't want her to think I am some sleaze bag, or make a fool out myself (guys get nervous too!) But I find myself coming up with excuses to go back and see her! Just to see her!
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male
reader, Sageoldguy1465  +, writes (26 March 2014):
 Here's a suggestion as to how you can "test the waters."....
Next time she contacts you for a project.... tell her that you will schedule it for the end of your day.... and the only "payment" you expect is for her to make you a delicious supper. THAT gives YOU a chance to learn if she has thoughts similar to your's.... AND also gives her a chance to rebuff you by saying something like.... "That's and interesting offer, but I think I'd like to just pay you, and that will close the book on the project that you will have done....
That gives YOU a chance to "ask".... and her a chance to express other than romantic interest... Give it a try.
Good luck...
P.S. When I do a project for my G/F, I ALWAYS present her with an invoice afterwards... but I have YET to see even the first penny!!!!! (.... but I do spend the night, when I'm done!!!!!)
A
female
reader, Flower89  +, writes (26 March 2014):
 My advice to you is I think she does like you,if she is flirting back and being sweet to you, but can I point something else out to you she is a 25 year old single mom, so I am assuming her income is tight, She needs work done in her home and met a guy she can wrap round her finger to do it. Sorry if am wrong there but I just don't see a attractive 20 year old, flirting as much with her guy older enough to be her father for any other reason. Than a meal ticket. I hope am wrong as u do come across as a sweet guy. Just keep your eyes opened.
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A
reader, anonymous, writes (26 March 2014): The age gap might be an issue but at the same time it might be nothing to her.
The only way to know is to just ask her. I mean, you need to stop going to see her without an actual reason so dating would be a good reason to go and see her, but if she says no, you need to stop going round to see her.
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