Ask Her Campus: Our Best and Worst Dates

With Valentine's Day next Saturday, you might be planning (or planning to be surprised by) an extra-special date night. But sometimes, even the best made plans have a way of spiraling out of one's hands and into the stratosphere. So with both cynicism and love in my heart, I asked the staff here at Her Campus to share the best and worst of their past dating experiences.

The Best:

1. I was hanging out with my friend (aka a friend I later had feelings for) at his house when it started pouring rain. I love rain, and he knew that, so he took an umbrella and suggested we take a walk outside together. It was such a simple date, just walking around the neighborhood and sharing an umbrella while talking, but it was the first time I got that fluttering feeling in my stomach for him and saw him as a gentleman, especially since he was holding out the umbrella to mostly cover me and not him. At the end of the night, I was nice and dry while he was soaking wet, but he insisted that I take the umbrella to walk to my front door. He put his hood up and ran home, and I remember thinking the whole thing was really cute.

2. My best date would have to be when my current boyfriend began the night by bringing me a bouquet of fake flowers (I'm allergic to real ones). He then told me that we were going out and he took me to a movie that he knew I had been dying to see, then to sushi, and then back home for some cuddling.

3. My best date was a trip to a San Francisco Giants baseball game. It was our first baseball game together and it was so much fun. We ended the night watching movies and eating. A simple, intimate date- the best kind!

4. I once danced with my boyfriend in high school in the middle of the street at night, I felt like I was Allie and he was Noah from the Notebook!

5. The best date I've ever been on was about a year ago when my boyfriend and I rode scooters all around Davis. We rode them everywhere: on campus, downtown, four different parks, etc. We raced and we had competitions to see who could do the coolest tricks. People stared at us, but we didn't care. We felt nostalgic.

The Worst:

1. My ex told me we were going out, but then he just walked me to the park so he could smoke. Then he asked for a ride home.

2. I just finished high school and a guy I was interested in asked to have a lunch date sometime after our graduation. I was 17, and he was 18. On our lunch-date, he spent almost all of our time together talking about his ex-girlfriend. He continuously praised this girl, and clearly wasn’t over her – which isn’t the end of the world, but an overall confidence-killer when you thought he asked you on a date because he was interested in you, too. Fail. Some of the things he said about her included that "she was the perfect dream girl" and "everyone liked her." It was awkward to hear since I was even friends with the girl! In the end, he eventually got over her and we kept in touch every now and then.

3. I once met a guy in an unfamiliar city. After finding my way across town and walking a mile in flats through dusty construction sites, I finally found him at a fish market. The whole block smelled terrible, the weather was awful, and it was once of the most awkward conversations of my life. He brought every topic back to economics (his major), didn't ask any questions, and would sing a song every time he stopped talking. I ended up wishing him a nice day after half an hour, and took the metro home. 

4. My friend and I were at the theaters and because I was nervous throughout the whole date, the gum I had been chewing turned soft. As soon as the movie was over, he turned to me and asked me to be his girlfriend, but when I opened my mouth to say yes, the melted gum came out of my mouth and onto the scarf I was wearing! I was so embarrassed that I ran to the restroom without giving him an answer. When I came out, a girl from our school saw us and asked if she could come with us to eat ice cream, and proceeded to follow us everywhere so he couldn't approach the topic again. I still cringe every time I remember...

5. My worst experience was NOT a date, but it was still probably one of the worst experiences I have had with [my boyfriend]. I was borrowing Hillary Clinton's new book from my mom and it was in my car. He is staunchly conservative/Republican and pretty much hates (not exaggerating too much) anything that has to do with liberals, and he has this absurd hate of Hillary Clinton. So he sees the book in my car and he refuses to get in until I hide it somewhere out of his sight. So he manages to piss me off with that from the get-go. We drive over to my dad's house (I was picking him up from his dad's), and we get inside. I choose to confront him about the book and ask him why he has to make such a big deal out of it. He just sits there and grumbles and ignores me, to which I say, "okay then, if you are going to be like that, then you can just leave". He promptly gets up and walks out the door. He actually walks back to his dad's, which is about 3 miles away. It took us about a day or so to make up from that. We almost broke up over that.

6. My worst date ever was on my ex's boyfriends birthday. First, I had to figure out how to fix his car's flat tire. The movie we watched was horrible, and dinner was a disaster because he was a complete jerk. The night ended with tears and a break-up, but it was one of the best decisions I ever made.

7. This year, I reconnected with someone I’d known since before I transferred to UCD. I hadn’t seen him or heard from him in a couple years – but last week, when I was on Facebook, I saw his name on the side list of possible friends to add. He responded to my request right away and messaged me. I was busy working on homework that was due the next day, but I chatted with him anyway. The conversation was nice, but he started talking about Valentine’s Day and dates. Warning lights should have gone off in my head right then, but I was getting stressed out with the homework assignment that I was nowhere near close finishing. I kept talking to him, but soon he started implying going out on a date and misinterpreting a lot of what I said. I barely knew him and didn’t want to go out, but his housemate sometimes snuck into the conversation to tell me he wanted us to go out. By this point, I felt I had to go out with him, but he wanted me to ask. So I did. The next day, however, I obsessed and worried over the date. I told my friends what happened, and they all agreed that I should get out of it as soon as possible. I ended up sending him a text explaining I didn’t want to go out with him. He said it was okay – on Facebook he deleted me as a friend.

8. A guy I’d known since high school came by my house with a Christmas gift: a rose. He also admitted that he had liked me for a long time and wanted to go out on a date. He was a sweet guy, very respectful and courteous, smart, kind – the only downside was that I didn’t reciprocate his feelings. There just wasn’t any spark when we were together. I told him I would go on a date with him, though I just wanted to be friends. The closest thing to a date we ever did was meeting up at the Coho for lunch for about 10 minutes.