I Had My First Experience with a Guy. Should I Ask Him Out?

Brian Rzepczynski
Brian Rzepczynski Updated:
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Reader Question:

I’m 30 and have had my first experience with another guy. We had a great first date, if you can call it that, but neither of us is looking to date – more of a FWB situation for the time being.

We got together a second time for dinner at my place. I didn’t think it was quite as exciting as the first time, but it was still good.

We’ve been texting – usually initiated by me – and have been working on getting together again, but his job has been crazy. I am trying to play it cool and wait until he texts me again, hopefully to make another date.

How do I find out what his intentions are with our situation? Is it OK to ask him flat out? How do I let him know I just need the reassurance that he is as interested in this continuing as I am?

-Jim (Pennsylvania)

Brian Rzepczynski’s Answer:

Dear Jim,

Yes, you are on the right track! Since we can’t read minds, the only way you’ll get a straight answer about where he’s at is to ask him directly.

It sounds like the two of you have been clear in defining this is a sex bud arrangement from the onset, but it’s a good idea to periodically check in to make sure everybody’s on the same page.

Based on the fact that you’re looking for reassurance, it sounds like you’ve possibly started to develop somewhat of an emotional connection. Is it possible you’re beginning to want more from this than a no-strings situation?

If this is the case, the time would be ripe for you to have this conversation sooner than later so your heart doesn’t become more invested if he is still only seeking an FWB arrangement.

A casual and simple “checking in” with you discussion should suffice here, and additional dialogue about modifying this arrangement if both of you desire this would come next. Good luck!

Dr. Brian

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