Online dating/telling them you like them-asking someone out

If you're using a dating site or chat room or the like to communicate, it's definitely on the table. If it's just a general discussion board or focused on something else (gaming for example) then the chance of it being date focused is much smaller and you'll probably need to actually get to the point of asking him out. What form that might take is mentioned below...

1. Well, somebody has to be...

2. Hrm. Based on past experience, I predict this question will get multiple answers split between 'age is but a number' and 'you're too different, forget it'. I tend to fall into the former camp and consider your age difference to be trivial (my partner and I have a 13yr age difference). I would suggest that it is more important that you determine your similarities and differences and overall compatibility. You may find that you just don't fit together or that your differences complement each other in lots of ways. Or some mix of the two that is still superseded by your feelings for each other (my partner and I have very different tastes in lots of areas (music, movies, reading, etc.) but also fit together really well and share similar tastes in lots of areas (some music, some movies, etc.).

All this said, you're currently just contemplating a first date. I'd suggest that determining if you both will even want a second one is probably a more immediate concern than how or how well you would fit together as a couple in an ongoing relationship.

3) Depends - Considering the shorter guy (that would be you), some guys really like being held by someone larger than them or being able to lean on their man without knocking them over (assuming he's not tall but very thin and lightly built and therefore would still be knocked over). Other guys may be bothered by feeling like they are at the bottom of well or something. Considering the taller guy - When I was in college/in my early 20s, I was as likely (sometimes more likely depending on my mood) to be attracted to a good looking shorter guy as a guy my height or taller (I'm just a bit under 6ft). For the most part I tended to consider the 'total package' of the way a guy looked and presented himself vs only one specific feature like height (and it's been said that differences in height become pretty irrelevant when you're both lying down anyway ). Ultimately, it's going to come down to his personal tastes and how well you both hit it off (which brings us back to this being a whole first date thing where these sorts of issues start being addressed on both sides).

Hm. Traditional - dinner and a movie

Slightly less traditional - coffee or lunch followed (or preceded) by something like a visit to a zoo or museum.

Maybe some sort of concert in the park or the like if you have access to those and you both like the same entertainment (actually for any of the above you probably need to discuss this since entertainment is going to be coming into it).

Some less advisable options:

The gym, paintball, or other activity in which you are in competition, either as a team or against each other. This can lead to emotions running high and not in a good way.

For a first date, you want someplace public.

My 2c worth,

Todd

 

Ok, so dating is apparently an option he's willing to consider, at least in principle. Just to clarify things here: You're actually working toward asking him out on a date vs. having already established that the two of you would like to go out on a date, yes?

Hmm. So what I'm hearing here is a definite maybe

So, what do you have in your area? What sort of cultural or social things are there where you live or within reasonable traveling distance?

Note that even coffee and a nice pastry or the like can make a nice first date. Or maybe a walk in the park afterward? Do they have parks where you live? The main point is seeing what resources you have available and then making use of them

If you both like paintball and both have the personality to make it work, then that might be an option. Hiking potentially runs afoul of the whole public space/first date thing, although I realize that in some places the hiking trails or areas are practically crawling with people.

Note that paintball may be lots of fun, but probably less opportunity for talking/getting to know each other. Although if you have things scheduled so there's time for that before/after that might not be an issue. Hiking should allow for both talking and activity.

How about just asking him if he'd like to get together for coffee/lunch/whatever? Your first post seemed to imply that you were already getting along pretty good.

For that matter have you actually spoken to him at this point (like a phone call/skype/hearing his voice)? I realize that I'm quite possibly simply revealing my age with this question and that text only communication may be perfectly fine with both of you

Given where it now sounds where you're at with this (and after thinking about it a bit), something relatively low key and potentially short (in case you decide things aren't working out) but with the option of being longer might be good. Coffee/lunch might be a good start with no scheduled anything after, but with some ideas in your mind if the issue of 'what do we do next?' comes up. That runs you 30min to an hour if you just order/talk/eat and then want to end things there. If you don't, then you could potentially go for a walk or just keep working through coffee refills and dessert or something and keep getting to know each other.

On a couple of final notes (since the forum kind of ate parts of your reply):

Being taller than you might make some guys try for a more dominant role. But its certainly not a given. He could just as easily be a really easygoing guy who is fine with 'going along with whatever' or be into a situation where you are both equal partners. Re the top thing, I once saw a 6'4'' guy lament "I have a prostate too, you know." Meaning that just because a guy is bigger than you doesn't mean he wouldn't be perfectly fine (or even thrilled) to take a more receptive role in that area if things get that far (at least sometimes, reciprocity is always good) .

I totally understand the whole overplanning thing. One of my mottos in life is that spontaneity requires weeks of careful planning. But as you say, this tends to break down when other people get involved. So maybe just try to relax and enjoy his company...

Hope this helps,

Todd

 

I think it would be best to have an activity planned with him in advance, rather than coffee and then no specific plan after. Coffee with no specific plan after might be read as a hookup rather than a real date. If you have social, semi-romantic plans, it is more obviously a "first date" rather than a one-time hookup.

On the first date, see what his post-college plans are, and find out if your lives are in a similar enough place for you to date. When you are with him, do you feel like an equal? Or does it feel imbalanced? I don't think 18 and 22 is automatically a problem. It only might be a problem.