Then Jack Happened: A “Yolo” Moment?


Question: Hey Jack, Alright… My problem is short and sweet. I’ve been dating this guy for a little over a month, he’s cool and we have a lot of fun together. Is he my soul mate? Probably not. But he has opened my eyes to a… we’ll say a new side of myself. Things are great and we’ve had a lot of fun, but now he wants to go from “50 Shades of Gray” to “Eyes Wide Shut.” Are you following me? Now, I know better than to do something I don’t want to do, or something I am uncomfortable with, but I am completely torn. It sounds intriguing and adventurous, but on the other hand – who does he think he is?!?! Am I being a naive for letting him manipulate me into doing this? I have been racking my brain with this and I can’t tell my friends about it. So should I (for the lack of a better term) YOLO it and just have a good time? Or should I preserve the little bit of innocence I have left and not open pandora’s box? Answer: I don’t think I can answer your direct “should I do it,” question any better than you can. It comes down to, which would you regret more: going through with it, or not. It’s good to be in a relationship with a partner that encourages you to expand your horizons and interests, so long as you’re happy and comfortable with it, but it’s up to you to determine if these new horizons and interests are directions you want to go. Getting involved with a guy that only likes to watch and play sports is a terrible idea if you aren’t interested in sports. But it seems that you do like sports, you’re just not sure how much. What I find interesting is the interplay of this guy and your new relationship. You say he isn’t your ‘soul mate,’ and chances are you’re right, but it seems that you do have some sort of feelings for him beyond the physical. If he was a sexy mannequin and this was strictly physical, you probably wouldn’t have written in. Simply, either you’d want to go there with him, or not. Your pleasant description of him and that you were a little offended by his ask seems to indicate that this might be more than just a physical thing, good long term prospects or not. You should sort out your issues with him before pushing the envelope on something you aren’t sure about. What’s the rush? This opportunity is not going anywhere. I’m not a prude, but in one month he has changed a very personal part of your life and asked you to participate in an adventure you’re not sure you’re ready for. This could be his manipulative MO: meet new woman, invite her along for fun, find next woman for party, repeat. He also could be very interested in you and wants to share this part of himself because this is his genuine article. You might have no real interest in him, but he’s fun and cool and you’d like to try this…and on and on. You might be fine with all this unknown, but until you can get a clearer view of, primarily what you want, and secondarily, what he wants, you should maybe hold off so your decision is as informed as possible. Also, talk to him about it. If you tell him you want to think about it, and he pressures you, then you know his intentions. With that knowledge you can make a clearer decision. If you are gung-ho regardless of what he says, and it sounds awesome, by all means dive in. Most importantly, if you do actually like him, don’t do something to simply appease him, that will likely result in regret. Only do (or not do) this for you. Remember, you can’t take back what’s been done, but you can always participate when you’re appropriately revved up and ready. Dear Delray, I am a one question a month kind of guy, so please send your trials and tribulations to and we can have some fun.