Chasing Kyle


A hypothetical:
Let’s say you are an attractive female in your 20s (not so hypothetical for you). You’ve had a handful of serious relationships in your past, the most recent one which ended about half a year ago. None of them lasted more than a year, but they all got fairly intense. You always got out when you realized there was definitely no long term potential and you’ve been the one to end each relationship. Guys tend to like you a lot and you’re usually in control. It’s nice, but you’ve definitely been burned by guys who seemed great on the surface until you really got to know them. Recently, it’s been hard to meet people, so you decide to give the online thing a try.

Within a couple of weeks of trying out the online dating thing, you meet a pretty cool guy, let’s call him Jake. Jake’s not exactly what you’re looking for, but he’s friendly, pretty attractive, intelligent and has an interesting background. You like Jake’s personality because he’s fun and shares some of your interests. You enjoy talking to him on the phone and can discuss random things with him for hours at a time.

You and Jake start hanging out pretty often. A few times a week becomes every other day. You’re a student, but your schedule is really chill so you can hang out a lot. You go out for dinner multiple times a week, see movies and concerts together. You like him more and more. You even start planning vacations together weeks from now. You like him enough that you decide to invite him to your family’s thanksgiving dinner 200 miles away after only being together two months.

But as luck has it, right after you invite him to thanksgiving, you get a call from Kyle. You’ve had a crush on Kyle since high school but he’s always been unattainable either because he wasn’t interested or was in a relationship. He’s known for years that you like him and this time, he calls you because he wants to try things out with you. You haven’t heard from him for a couple of years but he’s single and he’s been thinking about you. It’s too good to be true. EDIT: Let’s assume for the sake of this exercise that Kyle is genuinely a good guy and not a douchebag. He was foolish not to realize how awesome you were back in high school and has seen the error of his ways.

But what to do about Jake? You’ve been interested in Kyle for so long that you can’t pass up on this chance. Jake is ok but you definitely think long term prospects with Kyle are better so you need to end things. How would you proceed?

Choose one:

a. Bite the bullet and be honest and tell Jake about the entire situation. Hope that he understands.

b. Don’t tell him about Kyle explicitly but tell him that you’ve done a lot of thinking and while you like him, you think of him more as a friend, so you think breaking up is best. Start dating Kyle hoping Jake never finds out.

c. Exaggerate about some psychological and physical health problems that have been bugging you. Tell Jake that these problems have become so severe that you need to break up and take care of yourself. Start dating Kyle hoping Jake never finds out.

d. Start seeing Kyle while you try to sabotage things with Jake by acting flaky and mean.

e. Write in your own answer

If you were really in this situation (and weren’t an ideal version of yourself so don’t just pick A), what would you choose and why? Inquiring minds want to know…

–Loves multiple choice

For this question, AskAdri (that’s me) decided to do something different. I sat down with three friends over a wine tasting and discussed the situation.

Here’s the final conclusion:

So there you go. Our conclusion is to go with honesty, but not complete and total honesty. Tell Jake that you want to date other folks too, or that you’re not ready to move into something so fast. Don’t be too specific.

As you can see, there are different opinions, although we mostly agree—get out there. Chase that Kyle.