I (26F) have been spending a lot of time with this guy (32M), and things seem to be going well. We were acquaintances until around May of last year, when we started hanging out regularly as friends. Right away I knew I was interested, and, you know how it goes, I spent months wondering if he liked me back. It seems to me that at this age, there’s really only one reason for two people of the opposite sex to start hanging out regularly (to find out if you’re interested and if you see it going somewhere). The thing is, we’ve both been single for a looooooong time, and we both know exactly why; because we’re incredibly shy.
Last month he asked me to be his +1 to his work’s Christmas party, and, despite our awkwardness, it was really fun and we had a great time talking and getting to know each other better. Afterwards, he walked me to my car and then invited me to a party he was having the next week. When I got there, we got away from the crowd and talked deep into the night and he brought up the topic of previous relationships, and we both shared our emotional scars and our hopes for the future.
So now here we are. It’s been a few weeks since the party, and Valentine’s Day is quickly approaching. I’ve come to the realization that if I wait for him to ask me out, I’ll be waiting forever... and I’m thinking of using V Day to my advantage. I figured that if I ask him to spend Valentine’s Day with me, he’ll figure out that I’m interested. If he doesn’t want to spend it with me, I’ll know right away that he’s not interested in me and I can stop wasting my time. But if he does want to go out, I’ll see what the general vibe is throughout the day, and if I think he still hasn’t figured out that it’s a date, I’ll nut up and tell him how I feel (at the end of the night, just in case it doesn’t go well haha). And, if the feeling isn’t mutual, we’re both adults and he’s a very kind man so I’m not worried about anything worse than a polite declination.
Thoughts? Encouragement? I have NEVER asked a man out before, but it’s something I think all women (even shy women) should do once in their lives. If you’ve ever tried to make the first move and it went well, I’d love to hear about it! I could really use some motivational words to help me get over my fear and nervousness!