So... There's this guy

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I'm 32 years old, I've never been on a date, or been kissed. I've never really been super interested in a guy before now. But now there is this guy at work. We have a lot in common and I feel really comfortable talking to him. We talk everyday at work and have for 2-3 months.He's funny and smart, and seems to like my quirkiness. I really really like him. I know he likes me ( I've had 2 people tell me that he does). But he is 8 years younger than me and I have no idea how to precede. I am very self conscious and would never be able to ask him out, so how do I get him to ask me? Of course, if he does ask me out, then a have a whole other problem to worry about, but one thing at a time.

Hi Anelynn.

If you're unable to verbally ask him, then write a note saying "I like you. Would you like to have coffee (or whatever activity best fits the both of you) sometime?" and draw two boxes for yes and no. Then give it to him and see how he responds. It's simplistic and a bit childish, but it's straightforward and you don't have to engage in that game of giving hints and waiting for him to ask you out.

Do you have anything that needs fixed? If you can find something, ask him if he can help you out with it. hehe

Has he actually asked you out yet? If not, your panic is premature and pointless.

Your age difference is not much of an issue, its quite common. Try asking him more about himself when you talk to him, and see how he reacts. A good test question would be "Do you have a girlfriend?". He may be unsure about asking you out, because of your age and his lack of experience. He may think you are with someone, so a subtle hint would help with that. Since you work together, you can go for lunch or coffee during a break, as an unofficial date.

Most of the time I give this advice to other guys…but I never claimed that it's exclusively FOR guys, but rather it's for anyone who cares to take the initiative.

So you two have known each other for about 3 months? Cool. Ask him out. If you have no experience dating, here's how you do it: "Suggest" you meet up some place for lunch, or "suggest" going out for coffee/beer after work.

Before you get there, you need to cultivate interest in yourself. How do you do that? Be interested in someone else. Talk to this guy, find out what kinds of things he's into. You don't have to know a single thing about it. You don't have to say all that much. Get him talking about things he likes and keep him talking. If, say, he likes to play golf and you have no clue how to play golf, ask if he'd mind taking you out to a golf course and showing you how to play. Work with whatever he's interested in, whatever he enjoys, whatever he's passionate about. Beer, golf, polka dancing, whatever.

Culturally we're taught that it's polite for the man to pick up the cost for whatever it is you do when you go out. In YOUR case, though, if you take the initiative, be prepared to pick up the tab unless he insists on it himself. You are also older, and that carries some weight as well.

After 2 or 3 date-dates, start invading his personal space. Try holding hands. If that works out, turn up the heat on eye contact and get your faces closer together. That will invite him to kiss you and you'll be able to check that one off the list.

I often like telling the story about an inexperienced woman I knew way back when. When she was alone with me, her attitude was to simply let things happen. She basically just handed me the reigns, and that got her into a lot of trouble (which she didn't seem to mind much, btw. ). You're in a weird position at this time in your life, and I think what you need the most is for someone to tell you to go ahead and play with matches. It'll be more fun if you find some gasoline.

My Girlfriend is six years older than me although you would never know it. I would have never asked her out because of the age difference and would assume she would not be interested. Don't let your inexperience stop you: she also admitted that I am FAR more experienced than her (first kiss at 29!) and would have never suspected it not for how *ahem* hard it was to fit at first.

I wasn't sure if she was into me so when we were walking on an icy sidewalk I grabbed onto her and she leaned in. Took that as my green light and the rest is history! I would suggest a lunch date first: I have done that in the past with coworkers who I wasn't sure were dating material. They were not, but it was an enjoyable experience nonetheless.

This is an outdated idea, that came about because men used to be the sole provider, while women took care of things around the house. Now, both partners usually work, and share responsibility at home (they should anyways ), so the cost of a date should be shared equally...at least after the first few dates.

During the getting-to-know period, the person initiating should pick up the tab, or at least offer to pay.

Ok, let's get back on track, before I get myself into too much trouble.

Oh, don't get me wrong…I completely agree with you. Absolutely right, dead on about whoever is asking for a date gets the tab. The old-skool justification is probably some traditional chivalry. I think about it differently.

I look at it this way: Whoever does the asking is making a request that you spend a significant portion of your day or evening with him (or her, in this case). You are giving up your time, when you could be reading a book, watching your favorite chick flick, doing your nails, taking a bubble bath, etc. (for guys apply appropriate gender stereotypes--hunting, fishing, watching baseball, eating buffalo wings at Hooter's, hacking Gibsons, watching pro-wrestling/NASCAR/bull riding/female mud wrestling, whatever). Point is, you're carving out YOUR time to be with someone who is merely enthralled by your awesomeness and wants to borrow it for an hour and a half. The LEAST he (or she) can do is make it worth your time by doing something you enjoy and funding the whole venture.

THAT is a date, as in a date-date in the conventional sense, rather than a casual meet-up after work or over lunch (my working definition of "date" includes all of them, even the casual ones that people don't normally actually "call" a "date").

It's not about some medieval sense of chivalry. It's about showing your appreciation to someone for making time for you. Strictly my opinion here (and with all due respect to SilverStar), but I would GENERALLY take an insistence on going Dutch or the other person grabbing the check as an unfriendly act and I'd probably lose interest in her. As in, she won't let me be nice to her when I'm the one who asked her out…a spurned offer is a sign of trouble on down the road. Of course, it depends on the exact situation--I can make exceptions, but this is generally how I view it. If I ask you out, you accept, and we have a real date, you've already paid your half just by showing up.

One could make the argument that this amounts to buying an escort or prostitute, but I don't see it that way. Escorts and prostitutes provide a service. I get nothing out of this except your company. Buying dinner or tickets or whatever is a GIFT. I'm not buying/renting you…I'm just saying thanks.