A bad case of the dates: WC students share awful dating experiences

The summer after my freshman year of college, I had been talking to this guy who was my best friend’s family friend. When he realized I was in town, he asked me out. After a nudge from my friend (who was hoping for a good story), I figured it might be fun. 

He took me to a drive-in an hour away, so we made slightly awkward small talk the entire drive there. I remember we saw Jurassic World, and halfway through, we started making out. A lot. 

After a while, I was bored and took advantage of my friend’s texts asking me how it was going. I told him. “Oh look, she texted me...again...better answer it.” I texted her back telling her to keep texting me because the kissing was so awkward and boring, so instead, she texted him that I was having a “great time ;)” and to “‘keep it up ;).” 

Needless to say, the drive back was uncomfortable, plus I missed the end of the movie, but at least my friend got the good story she was looking for.

—Bored at the drive-in


So this was my senior year: My boyfriend and I of 3 years had just broken up, and he was spending Valentine’s Day with the girl that he broke up with me for.

An ex-boyfriend of mine had been contacting me since my break up, although he and I hadn’t spoken in years! He asked me out for Valentine’s Day and I made it clear that I was not ready to date again. He assured me that this was just as friends; casual, and to get my mind off of what happened. So I agreed. 

Valentine’s Day comes around and he picks me up with flowers, a bear, and chocolates! I am so taken aback, but I try to be nice and thank him, reminding him that this was just as friends. He agrees... awkward right?

He then takes me to an expensive, romantic restaurant overlooking a beautiful view. He has already called ahead and ordered dinner for us: the Valentine’s Special, which was $100 a person!!!!

At this point I was freaking out. I felt terrible that he was spending all this money and time on me, because I did not like him that way and was not ready to move on. I did not know what to do, but I could see that my hints at this being a “friend date” were not really being heard by this guy.

Dinner was so awkward! We hadn’t hung out in years and now we were in this romantic setting surrounded by serious couples!

I ended up resorting to talking about my break-up and my ex to try to convey how sad I still was about this, again making it clear that this was not a date for me!!

I texted my best friend at the time , asking for advice, and he said to make up an excuse for why I needed to leave, so I said I needed to go home to study (which was actually true).

A long silent drive home..... One hour drive.....

He pulls up at my house and hasn’t given up hope yet. He tries to kiss me in my driveway without my permission. Luckily, my bestie at the time pulled up right after and told my “date” that he should be going. Never seen a more tense moment! My friend saved me and I spent the rest of the night studying!!!

—Involuntary Valentine



I went on a date with this great guy — funny, handsome, intelligent. I invited him back to my house, he takes off his shoes and there is something wrong with his big toe. 

When I asked him what happened, he said, “I have a toe fungus but it’s only mildly contagious.” 

He texted me a few days later asking if I wanted to hang out again, and when I asked him if he finally took the medication for it he told me, “I have plenty of socks.”

—Fun with feet



I was a senior in high school and I went on a date with this guy who was almost nineteen, so, of course, I was expecting it to be super exciting. We decided to see a movie at the Whittier Village Cinemas on a Sunday evening and I got there an hour early because I was super nervous. But when I texted him, he did not reply. 

I started to think he was going to stand me up, but ten minutes before the movie started, he texted me saying he was almost there. He finally showed up —turns out he walked to the theater. I went in for a hug, and he pulled back and waved at me. 

He didn’t offer to pay for my ticket as he pulled out a bag of quarters and told me, “I like change...that’s why I like Obama, too.” Clever kid. 

During the movie, he didn’t talk to me or make any moves. Then, when we left, he guilt-tripped me into driving him home and didn’t even say ‘thank you’ when I dropped him off. We are still friends and alk, so there are no hard feelings. 

—Chump change



I was in high school and this guy asked me out for dinner. I assumed he meant going out to a restaurant —  I didn’t know he meant physically making me dinner. 

He made me Top Ramen — basically my college diet today. His parents came home from work, cooked their own separate meal, and sat down to eat at the same table. 

It was awkward. They asked me questions about my family and myself. His parents and I talked more than he and I did. I think he felt awkward. 

Ramen and the ‘rents



I had paid to fly out to D.C., and was there for five days. He’s in the military and the Marine Corps ball was the Friday I was in town. He knew I would’ve been there, but chose not to bring me because he hadn’t told anyone we were dating. 

I saw him Saturday night. He was three hours late meeting me, and when I woke up in the hotel Sunday morning, he was gone. 

We had plans for most days, but I ended up only getting to see him for about twelve hours. 

—Dateless in D.C.



In middle school, Valentine’s Day was a huge deal. We transitioned from Valentine’s Day cards to more of a grown-up gesture of love. 

During the first week of February, our school was selling Valentine’s Day grams where students were able to send a card and a rose to anyone they wanted.

So in the sixth grade, I was given a Valentine’s Day gram, andthe note said it was from a secret admirer. Throughout the day, I was on the lookout for who sent me this rose; my eyes and ears were on high alert for who it could be. 

The next day, after realizing I was unsuccessful in the search for this secret admirer, I came to find that some of the girls in my class sent the rose as a prank. So, naturally, when the next year came around, and Valentine’s Day grams were being distributed once again, I hoped not to get one. That wasn’t the case. Instead a boy in my P.E. class came up to me and asked me if I sent him a Valentine’s Day gram and I responded no. He showed me the card where someone wrote “From your secret admirer.” 

I told him that it I didn’t send it, and he accused me of lying. Later that day, I found out that it was his friend who wrote the card because he thought it would be a fun prank to pull on the guy. 

From that day on, I was always arano id of receiving a Valentine’s Day card because I always felt like it was an excuse to prank other people. 

— Your not-so-secret admirer