Started as a Hookup, But I Caught Feelings


I recently made the mistake of catching feelings for this guy I hooked up with.  About four weeks ago, I started messaging this guy on Jack’d and we met up with the intention to hookup only.  Let me tell you, after round one I was extremely satisfied. When round two finished, I was in awe.  Needless to say, he was definitely feeling the sex too. Well since that first night, we have been staying in contact pretty regularly, and hook up at least twice a week, if not more.  Having gotten to know him a little, I find myself falling for him.  The thing is, he has made it clear on his Jack’d profile that he doesn’t want to be in a relationship.  Heck, he’s even told me he loves being single.  I guess what I’m asking here, is what do I do here?

Thanks in advance bro, and love the site btw.

Restless in Philly

Dear Restless in Philly,

Thanks for writing to me and sharing your kind words about the site.  I always appreciate a good compliment.  Now as far as your dilemma here, it’s one that is quite common in both the homosexual and heterosexual communities.  It takes a special kind of person to have routine sex with the same person and not catch any feelings.  So if you find yourself not being that kind of person, don’t worry.  They are far and in between.  In fact, you would be in the majority on this.  As am I to be honest.

Based on what you told me, you in fact did make a mistake here. If you wanted to keep things on a “sex only” level, you shouldn’t have made a conscious effort to continue to get to know him.  You should have learned his name, his status, and whether he is sane, and that’s it.  It’s too easy to get wrapped up in a person when you find out you and him have more in common than your healthy appetites for the male anatomy.

Now I’m going to advise you to do some self-reflection and analyze your emotions here.  Ask yourself if you are really catching feelings for this guy? Or if the feelings you think you have are really you being sprung on a good “funstick” and/or on good “box”?  The latter is totally possible.  Some people will argue that good sex is hard to come by.  And you’ve apparently found some.  Those same people may say you just want to make sure it doesn’t get away from you.

If after doing some self-reflection, you realize that you are in fact falling for this guy, then I say tell him.  “Closed mouths don’t get fed.” LOL!  Meaning, if you never speak up and tell him how you feel, then you’ll never know if you can be the one that sways him to give up his “singledom.”

Suggestions going forward.

  1. When you talk to this guy about your feelings, under no circumstances should you say you’re in love. After a month of dating, saying the L word will scare most people off. Simply say that you are vibing with him, and allow the conversation to move on from there.


  1. Don’t be too discouraged if this man doesn’t want to date or be in a relationship. His desire to be single may be too strong for anyone, including you, to overcome.

As always nothing but love,


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2 thoughts on “Started as a Hookup, But I Caught Feelings”

  1. Restless in Philly says:

    Well I can’t be mad at your advice here. Dead on the money!

    1. AsAccordingToT says:

      Lol Thanks. Glad you like it

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