Fun Dates are Fun Because They're Fun

Back again with another question this week, from one of you. If you haven't asked something but have a question burning on your mind, please take advantage of the anonymous comment option below and leave it for me! I'm really enjoying hearing what's on everyone's mind.

Today's question comes from K:

Rachel, how do I make dating fun? Do I Clockwork Orange myself with romcoms until I am convinced something like that can happen to me? Or more specifically, how can dating be more attractive to someone who is not socially inclined other than "if you don't do it, you'll be alone forever"? 

Also, how to politely tell my parents that I do not need them setting me up with their friends' children?? Last time I checked arson was a felony??
K

This is tough, K, because ultimately dating is a social activity, no matter how you spin it. And if you don't want to be set up, you're eliminating one of the simplest ways to get around the hardest part: meeting people.  So although my advice on the parent-front is to tell them you're a grown adult and you're making the decision you don't want to go on any more of their set-ups, realize that you are limiting yourself if you do that. After all, just because the first few were duds doesn't mean the next one might not be the guy/gal of your dreams. Personally I'd love it if my mother knew someone to set me up with. She has great taste.

With that understood, you asked how you can make dating fun even though you're not a social butterfly. My answer is the same for extroverts, but I think it becomes more vital to the experience if you're an introvert. Find places to go and things to do that make you comfortable.

Earlier this year I was talking to a guy on Bumble who was a competitive golfer and who was encouraging me to get "back on the course"—I haven't gone golfing since I was about 8 years old. He had a perfect opportunity to ask me on a first date here. He could have invited me to go golfing to re-teach me some of the basics. There are so many reasons this would have been a great first date:

• SHOWING OFF. Mr. Tee-Off would have been inviting me to do something he loves and is good at. Let's face it. Dating is a lot like a job interview. Showing off your strengths is not only part of the fun, it makes you more likely to get hired. It's a turn-on seeing someone at their best.
• MEMORABLE. This would have been such a unique first date that I would have found myself anticipating and looking forward to (and maybe getting a little nervous about—but good nervous). I would have told all my girlfriends and maybe a family member or two "Yeah I meeting this guy to play golf," and I guarantee they would have been calling me afterward to find out how it went.
• EASY CONVERSATION. Because there was an activity built into this date, even if it's going horribly and we're not clicking at all, there is still an obvious conversation topic to fall back on: golf. It's the same reason I recommend going to a movie and then dinner. You can talk about the film while you're eating. If you're not overly-comfortable making chit chat with people (or like me, you just hate small talk), activity-dates are a great way to go. You don't have to constantly talk, and when you do, there is something ready-made to discuss. And by "activity" I don't necessarily mean something outdoors-y or athletic like golf. Museum exhibits are another great example. You don't spend every second talking but you can strike up conversation when you see something you have strong opinions about.
• COMFORTABLE ENVIRONMENT. Personally, I'm attracted to confident men who put me at ease. It's a lot easier to do that for your date if you take them someone where that makes you feel relaxed. Mr. Tee-Off would have been right at home on the green. 

Another example, this time a date I actually did go on, would be my first date with Mr. Mess. Mr. Mess was a serious audiophile and collected a lot of vinyls. He took me to his favorite record store where we talked about our favorite music for well over an hour. The guys who worked the counter knew him by name and liked him a lot, which made him look like a little bit of a big-shot (or a hipster, but whatever). Afterward we went and had a cup of coffee where I got to talk about all the reasons I love coffee, as well as continuing our music conversation. We had a great time. He also made me feel special by telling me that record store was one of his all time favorite spots in the city and that he normally didn't take people there. I'm not saying you should violate your shrines or that you should lie and feed every girl that line, but if you feel comfortable taking someone to one of your favorite places, make sure they know it's special to you. It will make them feel good.

Even as an introvert, I'm sure you can find places where you feel in your element. Ultimately, the right person will enjoy these places with you and help make you more comfortable by balancing things out. You probably need someone who can fill the gaps in conversation but still enjoys comfortable silence. You'll recognize them when you meet them, promise.

P.S. Please don't clockwork orange yourself with Romantic Comedies. Most of those plots would go terribly in real life. (Be sure to read the hover-text on that comic.)