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Need Dating Advice on Pursuing a Crush

Hi April, There's a guy that I had a leadership program with last year and we developed a friendship through the program and the latter part of it I started to develop feelings for him and a crush, probably because I felt like there was some chemistry and flirting going on. But we were never around each other outside of a professional environment. A month after it ended, I emailed him to give him (and everyone in the class) my new contact info because I switched jobs. He mentioned that we should get lunch and catch up but that fell through. a month ago I contact him for that lunch (since we were working together on charity tournament) and He seemed excited and the lunch went very well and he told me that he wanted to do it again soon. A couple days later, I texted him saying it was good to see him and we held the convo for a little bit but it didn't go anywhere. I was hoping he would ask me on an actual date, but that never happened. We just had the tournament yesterday and we worked it for about 12 hours and I felt like he was flirting with me and had chemistry. He would make jokes at me, and come over and talk to me any chance he could and made a effort to involve me. I'm just so happy around him and want to continue to progress and make sure he knows I'm interested. I don't want it to seem like I'm chasing him but I want to see him again and even start dating but I'm not sure how to do that since I already felt like I put myself out there by asking him to lunch. Would appreciate your advice!

Re: Need Dating Advice on Pursuing a Crush

Boy, you've done everything right... and he's not taking the bait. Sometimes, a guy just isn't ready when you are, or he's not as interested as you are. It sounds like yesterday went really well, and the flirting is a great sign. Maybe he's getting ready to ask you out. But.... for now, the ball is in his court. When you do see him, focus on flirting and not on friendship. Make sure he knows that you're interested in him romantically. That means taking out all platonic messages. You might be surprised at how guys really need encouragement before risking rejection by asking you out. They get nervous that you'll say no, and some really need a lot of encouragement. You may think he knows you like him, but he may need more cues from you in that department. Definitely don't invite him out again -- it's his turn, and his move should be a date. So, increase flirting when you see him, and try to keep the rest of your life busy and interesting so you don't end up appearing needy or desperate. If you do all that and he still doesn't ask you out, move on. But for now, I think that because your day, yesterday, was so promising, he may be getting ready to ask you out. Fingers crossed -- and if you have any other questions, I'm here!
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.