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I know that this likely sounds like a silly question, but here goes nothing...
About two weeks ago, I noticed that someone had right-swiped my OkCupid profile. When I saw who I had matched with, I was shocked: not only was this woman beautiful and tall, but she was also interested in architecture, sustainability, urban planning, and city living! She is also a college graduate (from a prestigious school), currently has a position, and is studying to go to med school. She is a woman who I would typically consider to be “out of my league” (though I need to stop thinking that after losing 104 pounds, graduating college, and getting hired at a well-paid position); nevertheless, I messaged her and we started talking. Here is how each of our dates went:
Date #1: About a week who, I suggested that we ride bikes and grab craft beer in Northwest Philly. We both took the train to Manayunk, met at the station, and spent the day riding our bikes along the Schuylkill River Trail. When we completed the trail, I showed her around Philly’s University City neighborhood. Afterwards, she wanted to grab dinner. We ate in Chinatown before walking around the neighborhood and eventually departing after riding the El together. We ended up spending about 6 or 7 hours with each other in total.
Date #2: Tonight, I took her to the tallest beer garden in Philly. We ate, each had one drink, and started to go deeper into what we had mentioned during the first date. We spent about an hour and a half walking together after the beer garden trip.
On each of the dates, she seemed to show signs that she liked me. She smiles, looks me in the eye, rarely checks her phone, laughs at my stories, and has consistently been the one to suggest that we do more than I had originally planned. She has also picked up nearly as much of the overall tab as I have put down! With tonight’s outing, she was physically closer to me than she was on the first date!
I’m planning on asking her out for a third date, but should I let her know that I like her now? Should I wait until after that third date has concluded? This is going to sound beyond ridiculous, but I have literally never had the urge to pursue a woman in my 22 years of life. The women I’ve gotten with in the past have each liked me for some period of time, but the one I’m seeing now is different. Although I’m physically attracted to her, I don’t want her just for sex; instead, I’m attracted to her because she’s the most intelligent, good-natured, cultured, quirky, smiley, and kind person I’ve ever taken on dates. The only reason I’m asking this question is because I don’t want her to end up being just a friend, but I’m not sure if she considers what we’ve been doing as “dates.” Her profile indicates that she’s interested in a relationship; however, I started taking her out under the guise of showing her around the city.
I think she's figured out that you like her, otherwise why would you ask her out?
What exactly are you asking us?
I was asking whether I should tell her that I like her before or after the third date I plan on taking her on. I feel like I need to tell her since I don’t want her to end up seeing me as just a friend (if possible). When we first started talking, I offered to “show her around the city” since she’s new here. I guess you’re right that she has figured it out, but I just want to be sure.
Quote:
Originally Posted by deepsix
If you met on a dating app, I don't see how there's a lot of room for confusion.
Only because her profile indicates that she’s also open to meeting new friends. I want to move towards being her boyfriend, not just a friend.
Quote:
Originally Posted by Rocko20
You don't tell her you like her, you show her.
This isn't 1st grade.
I understand, but I’m scared of rejection in a way. I’ve also been hurt by women I’ve taken the time to show that I like. I don’t think she would hurt me, but I guess I was just looking for reassurance when I posted this last night.
By showing, not telling... When you tell, you might be rejected.
BTW: If you are SO afraid to get hurt, maybe you should get some therapy before you start dating women? They will sense your fears a mile away... and believe me - it's not appealing.
Quote:
I want to move towards being her boyfriend, not just a friend.
I was asking whether I should tell her that I like her before or after the third date I plan on taking her on. I feel like I need to tell her since I don’t want her to end up seeing me as just a friend (if possible). When we first started talking, I offered to “show her around the city” since she’s new here. I guess you’re right that she has figured it out, but I just want to be sure.
Only because her profile indicates that she’s also open to meeting new friends. I want to move towards being her boyfriend, not just a friend.
I understand, but I’m scared of rejection in a way. I’ve also been hurt by women I’ve taken the time to show that I like. I don’t think she would hurt me, but I guess I was just looking for reassurance when I posted this last night.
You ask her out on the third date, and as you're walking around together, you brush her hand with your hand, and if she doesn't move away, then you start holding her hand. At the end of the date, or at another opportune time, you kiss her.
Bada boom, bada bing.
Some folks consider the third date the sex date.
It seems to me, that at this juncture, it's up to you whether things go in the friend zone, or not. Try holding her hand, and see how that goes. If it goes well...go for the kiss. You already said that she's voluntarily extended the dates, and suggested things. Dude, she likes you.
Find a moment alone with her and grab her by the hand, then kiss her
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When you tell, you might be rejected. 
