OK. just reading Canadas laws. (copied for reference)

The age of consent for sexual activity is 16 years"

However, the age of consent is 18 years where the sexual activity "exploits" the young person -- ....Sexual activity can also be considered exploitative based on the nature and circumstances of the relationship, e.g., the young person's age, the age difference between the young person and their partner, how the relationship developed (quickly, secretly, or over the Internet) and how the partner may have controlled or influenced the young person. Are there any exceptions to this?

The Criminal Code provides "close in age" or "peer group" exceptions.

For example, a 14 or 15 year old can consent to sexual activity with a partner as long as the partner is less than five years older and there is no relationship of trust, authority or dependency or any other exploitation of the young person.

Althought what you're doing is legal, still in dodgy waters if it falls below whats considered above.

I can't pin point if your age is a reason but I can imagine most girls openly wont want to be seen to go for a guy a few years older, even thought theres plenty who will, and some who openly will. I never gamed when i was 17 but I have had plenty of girl friends who said they lost virginity to guys twice their age when they were teenagers (which is frankly disgusting but thats life)

Be very aware girls can demand/do things under the influence of alcohol they later dont remember and make accusations later. Protect reputation.

In terms of where to find good wingmen, gravitate towards the popular/cool guys, and stay away from losers even if that means distancing from any loser mates. Raise reputation.