Do I sit back and wait or take the lead?
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| Sat, 10-01-2005 - 8:42pm |
I feel so silly even asking this...I am a grown woman in my 30s. But I back in the dating scene after many many years, and sometimes I am just lost, so please forgive me!!!
There is a man that I see everday on my way to work. His family owns a small business that I stop in for my daily caffine fix. What started with friendly hellos has turned into more in depth conversations at times...and I would hope so since we see each other 5 days a week!
I have gotten the feeling that the last month or so he has been flirting with me. But, like I said before, it's been so long I probably wouldn't know a flirt if he walked up and planted one square on my lips!! (Well, maybe I'd get THAT one) I happened to mention this to my friend I have started commuting with...and they told this person I "thought they were hot". I almost died, but then had to laugh at the whole thing.
This man actually replied he thought I was pretty as well, and the other day we were all talking and he made another reference to the fact that he thought I was very attractive. He also has told my friend, without provocation this time, that he thought I was a sweet woman.
Is this professional courtsey or genuine flirting? If it is the later, why hasn't he asked me out yet? I would love to have the nerve to ask him out, but I wouldn't even know where to start. Remember, we are in a business setting, and I am his customer.
Any insight would be wonderful!

Normally I would say go for it, but I am a little hesitant because this is a coffee shop and banter with the customers is highly encouraged, this is the way coffee shops keep their clientele.
I'd keep having friendly conversations with this guy for a few more weeks and listen closely to find out whether he has a wife/girlfriend, or if he starts comping you your coffee.
That's tricky to me. Either you use up ur time thinkin and wondering what's up, only to know in the end that it's a dead end, OR u talk to him lightly and nicely and directly and (perhaps) know it rightaway. I know, easier said than done. His mentioning that you are attractive and sweet certainly sends the signal that he likes you. I personally feel those comments are a bit more than casual and friendly. You could always venture and suggest coffee together some day. Nothing to lose there. With that step, you will come out with more information certainly. It is up to you..
Goodluck!!
Between being casual acquaintences and proper dating, I think there is a middle path of "friendship" that you could take. If he likes you, and you like him, and he is not seeing anyone else, he might not mind a friendship. Whether or not he is ready to date, I am sure he could have a friend in you. Neither of you need to "jump headlong" into anything at this point. This way, even if you meet him everyday, it won't be awkward. You'd only be building on the friendship and goodwill.
If it's a "fear" of tomorrow stopping you, (incase things don't work out) then it's not a good idea to hold back, when you don't want to. If you seriously want to get to know him better, then you should not hesitate. Let tomorrow be taken care of when you get there. In my opinion.
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If a man is truly interested and he sees you every day, why wouldn't he ask you out for coffee atleast?
He does sound like he's flirting just a little and might enjoy seeing the o.p's reaction.
I've put myself in this situation with someone I felt was flirting with me and I saw him about every other day. Low and behold, my phone rings and he says, "What are you doing for lunch?"
Why can't he do that if he's interested?
I'm not one to ask anyone out. I did once and he accepted but I think it was more of him being polite than interested.
I'd never ask anyone else out, though. My thing is if I'm interested in someone and I'm giving him all of the signs that I am, then it should not be a problem for him to ask me out unless he's either not as interested as I'd like him to be or he's just not available.