Ask to see Will one on one for coffee or something.

mrsconn23

Dear Prudence,

I am a 24-year-old woman who has exactly zero experience in dating. A couple of guys have expressed interest in me in the past, but I turned them both down because I didn’t want to be more than just friends. I never even had a crush on anyone before I met this guy “Will.” With him, I feel like I’ve finally met someone I could see myself dating. He’s kind, sweet, and hardworking—everything I admire in a man. We’ve been a part of the same social circle for over a year now, and I’ve always liked him, but now I really like him, and I can’t be sure but it seems like he might like me too. He offered to be on my team during a game night when I lamented my lack of skill, and he made a point to remember my birthday and text me, while everyone else in the group forgot. How can I show him I’m interested in him without being too overt and making a fool of myself if he doesn’t really feel the same way?

—Crushing for the First Time

short+sassy

The LW won't like my answer, but she needs to step out of her comfort zone and ask him out on a date.  Clearly a romantic date.  No being wishy-washy and phrasing it in a way that could go either way (friend date vs. date-date).  Or at least telling him on the date that she's interested in him, if it seems like it wasn't obvious.  

He may not feel the same way and that's the gamble.  But if he says something like that. reassure him she understands.  That she's still glad to have him as a friend and that's also fine.

Sure, it will be a bit awkward.  But it's the worse-case scenario and isn't even that bad.  As long as it's not too hard for her, they will stay friends and the awkwardness will go away with some time.  

charlotte989875

Ask him to coffee/ a drink/ a museum. Be clear it’s just the two of you. 

There’s no way around the risk that someone will say no. You take the risk and see what happens. 

mrsconn23

He's remembering LW's bday.  I don't text people happy bday unless I *really* like them (friends only, clearly...LOL).  I think it's pretty low-risk that he'd say no to meeting up with LW one on one.  

Anyway, there's no way to be 'risk-free' here, but I think LW is overthinking it.