"April Masini answers questions no one else can and tells you the truth that no one else will."

I made out with my boss…and now its awkward

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  • #2624
    Anonymous
    Inactive

    April,

    I started an internship at a local baseball team for the summer at the beginning of June. At our second game, I met a fellow co-worker named Ryan who immediately introduced himself the second he saw me. At first I assumed he was an intern as well, but later that night at the meeting I found out he interned last summer and is now technically one of my bosses. He just graduated college and I am about to start my junior year.
    There was some definite sexual tension and a few glances here or there. But, because all the other interns were attracted to him as well, I assumed it was only on my side. A few weeks later after some other co-workers added him on Facebook, I added him as well, figuring that nothing would really happen organically at work because we never get the chance to talk. Almost immediately, and to my surprise, he messaged me on Facebook. We chatted for a while, with obvious flirtation. He messaged me again the next day. I was teasing him about his job of raking the field and doing the grunt work after the game. He asked if he was at least the hot yard guy that older women fantasize about in TV shows. I told him that everyone around the office calls him Hot Ryan. He asked what I thought. I said I may have picked up the nickname as well. He said the attraction was mutual. Everything was very forward. At one point he joked around about trying to “woo” me. He left his number for me on the chat when I said I had to go.
    I told him I had a party to get to after the game on Wed, so I had hoped it would go quickly. He jokingly said ‘thanks for the invite’ and pretty much invited himself along, which is what I had hoped for in mentioning it. We exchanged knowing glances and a few texts during the game that night. I told him the address of the party and left with a few other interns. He had to stay behind and finish his work but said he would do his damndest to get out there. My friends and I left the party after a while, by which point I was definitely tipsy, and we went to a few local bars. He made a point of continuing to text me when I asked him if he was still coming. He went home, took a shower, and offered to pick me up from the bars. I told him I didn’t really want him to see me when I was drunk. He assured me it was fine. He came and picked me up around 2 a.m, drove me to my car to get my house keys and took me home. Nothing happened at all. Just casual conversation amidst sexual tension. He dropped me off. I texted him a few minutes later thanking him for the ride. He texted back saying it was no problem but that we “hadn’t explored any sexual tension. Just throwing that out there 😉 “
    I told him to just grab me tomorrow and we would…explore. Then I realized I had work at noon and no car. He said he was still in the truck. I told him he could turn around if he wanted but that I doubted he would. He did. Keep in mind I’m a little drunk and he is stone cold sober. He called me, and said he was outside. I went downstairs, and was a little surprised to find him in my yard and not his truck. He grabbed me and kissed me. We made out for a little while in the yard and I thought it was amazing. Our lips connected perfectly and he was a much a better kisser than any other of the 20 or so guys Ive kissed. I stopped him and said we had to get my car, but that I probably needed to still sober up a bit. He said he would “take care of that”. We got to the street my car was parked on but he pulled off onto a dead end road just before my car. I asked him why we stopped. He said to “sober me up”, chuckled a little bit, and then kissed me again. We made out in his truck like a Taylor Swift video for about an hour.
    It came up in conversation that I was still waiting and he had had sex with 3 girls. Did not seem like a big deal, though I think he might have been surprised. I never said I was waiting for marriage, in fact he asked and all I said was the perfect person. We didn’t go far at all. Shirts came off and making out was all. I told him I had to leave so things wouldn’t go any further. He wanted me to stay. But, after I left he texted me almost immediately telling me what a good time he had and continued to flirt. He did say “so agreed no one at work should know?” I, still tipsy, said “ummm…well you obviously don’t.” Now, I had gone out with fellow interns that night that had seen me get picked up by him, so of course they knew something had gone on. This is the only possible weird thing I think of that may have gone wrong, the fact that some co-workers know.
    The next day, Thursday, we had another game. We exchanged glances and a few texts again. I didn’t expect to hang out with him the next day at all. We had a game Friday as well, but he seemed intent on avoiding me completely. I texted him once during the game about a creepy host family dad (they volunteer to host the baseball players in their homes during the summer. Free boarding and food) who had gotten a little too drunk and given me his address and phone number so I could “come back to his house and he could offer me up to the players” who were having a party that night. It was creepy and since Ryan was in charge of the host family’s I texted him jokingly but at the same time kind of wanted him to come over and protect me a little bit or at least text me back. Neither occurred. My brothers name is Ryan as well. Which he knew. I accidentally texted baseball Ryan instead of brother Ryan to ask if him and his friends were going out that night. Immediately texted baseball Ryan back and said sorry wrong Ryan. He said “haha its cool, Im in bed right now.” I texted back and said “yeah I figured you would be. You looked exhausted after the meeting, Do you at least have the weekend off?” “Yes ma’am”. I, again a little buzzed after a Friday night in a college town, said “well in that case maybe we can repeat wed night”. No response on Sat, Sun, Mon, and now Tues. I didn’t text him again. Waiting to see if hell ever text me. We have games on Thurs, Fri, and Sat this week. Im not really sure what to do. Should I just let it completely go, or does he possibly still like me?

    I guess what I’m trying to ask is did I do something wrong? Does he not like be because I was drunk, even though he made a point of coming back to get me, knowing
    I was drunk? Is it because hes my boss and hes just now realizing any implications with that? Is he playing it cool? Or is he just not that into me. I don’t understand why you would declare your attraction, make out with someone, text them immediately after, and then never again. Unless something went weirdly wrong. Sorry for such a long message, but I figured you needed the whole story and any enlightenment will help. Also how should I confront him, if at all, at work when I see him? Ignore? Or say something like “So the chase is over, and now we ignore eachother?” Or play it cool and casual and just ask how his week has been?

    Thanks,
    A

    #13998

    It’s always hard when YOU think things are going swimmingly and HE isn’t all that interested any more. When this happens I have readers writing me desperately trying to figure out what went wrong and why someone who seemed interested, has now lost interest. Well, it happens. He was interested — although I’m not sure he was interested in more than a sexual thing — but now he’s cooled and isn’t showing any signs of wanting to date you. 😳

    When this happens it’s a mistake to CHASE him. Women should never chase men because it ALWAYS backfires eventually. What you can do is be your same alluring self, and if he IS Mr. Right then he’ll go after you, and if he isn’t — you’ve dodged a bullet and haven’t wasted any time investing your energy in someone who isn’t going to pan out as more than a fling.

    All the reasons you offer up for his cooling down are possibly legitimate, but the bottom line is that he has cooled and you are free to pursue other guys.

    I hope that helps. And you know, you’re not too young to get the dating low down by reading Think & Date Like A Man, a book I’ve written for women who don’t want to make mistakes (like meeting up with a guy at 2 a.m. when you’re tipsy and going parking to make out only to find no second date materializes! 😳 ) and want to treat dating as if they want to win the guy! It’s a short read that downloads immediately and I think you’ll benefit from it. Here’s the link: [url]https://www.askapril.com/relationship-dating-advice/think-and-date-like-a-man.html[/url]. Let me know what you think.

    And join me on AskApril.com on Facebook at this link: [url][/url] — I want to see you as one of my members on this group page! 😀

    #14422
    maelene87
    Member #14,058

    April is right don’t chase let him come to you 😛

    #14501

    Thanks, [b]maelene87[/b]!! Hope it works out for her. 🙂

    #47904
    Ethan Morales
    Member #382,560

    Ryan came in hot fast flirting, late-night pickup, physical tension, all that. But that speed wasn’t about connection, it was about chase energy. He wanted to feel wanted. Once that high hit its peak when you kissed, when it became real the mystery was gone, and he pulled away. Guys like that often mistake attraction for intention. They’re not lying when they say they’re into you; they’re just not built to stay once they’ve satisfied the curiosity.

    He wasn’t just another intern; he was your superior. That added weight risk, reputation, potential consequences. When he realized coworkers might’ve seen or guessed something, panic probably hit him. It’s one thing to flirt over messages; it’s another to realize the people around you might start talking. For someone fresh out of college trying to look professional, that fear can override genuine attraction fast.

    You were open, flirty, a little drunk human. You didn’t pressure him, you didn’t cross lines; he made the choice to show up, drive over, and initiate. If he’s now ghosting you, that’s on him, not you. Don’t rewrite the story like you’re the problem. The truth? He probably liked the chase but wasn’t mature enough for what came after.

    Right now, he’s probably trying to avoid discomfort at work, in conversation, or facing how he handled things. It’s not that he suddenly hates you or regrets everything. It’s that he’s uncomfortable facing the emotional weight of his own actions. A lot of people confuse silence for rejection, but sometimes it’s just cowardice dressed as calm.

    If you bring it up directly, he’ll likely get defensive or try to downplay it. But if you act grounded, professional, and cool around him no bitterness, no chasing you’ll disarm him completely. That’s how you regain control of the situation. Don’t give him the satisfaction of knowing he got under your skin.

    Never confuse attention with intention. What a man does after intimacy emotional or physical tells you who he is. Ryan showed you he’s not consistent. That doesn’t mean you can’t enjoy flirting or chemistry, but next time, hold back a little and see if his interest survives the waiting. Real attraction doesn’t vanish after one night.

    He’s not coming back. And that’s a good thing. He wasn’t built for anything real right now still immature, still playing at being the charming “hot guy.” Let him be that. You? Move forward. You’ve got emotional awareness he doesn’t. Keep that, protect it, and next time, don’t let someone earn your vulnerability before they’ve shown consistency.

    #49850
    Tara
    Member #382,680

    He was interested enough to kiss you in a yard at 2 a.m., interested enough to drive back when you practically dared him, but not interested enough to follow through once the thrill wore off. He got the ego boost, the chase, and the validation. The second it shifted from spontaneous fantasy to real-world responsibility, he bailed. That’s not mystery that’s male predictability at its most basic.

    You didn’t “do something wrong.” You just assumed intensity equals intention. It doesn’t. He liked the moment, not the implications. Once sobriety, workplace dynamics, and potential consequences kicked in, he did the only thing men who lack backbone always do: he hid. Ignoring you is his cleanup strategy. Not because you were drunk, not because interns saw, not because he’s suddenly noble because he cares more about avoiding complications than he does about you.

    Don’t text him. Don’t chase. Don’t ask what happened. At work, you look him in the eye, give him a neutral “hey,” and move on like he’s a background extra. The second you hint at hurt feelings, confusion, or nostalgia, you hand him power he absolutely doesn’t deserve. He already showed you exactly where you rank in his priority list somewhere beneath convenience and above accountability.

    #49851
    Tara
    Member #382,680

    He was interested enough to kiss you in a yard at 2 a.m., interested enough to drive back when you practically dared him, but not interested enough to follow through once the thrill wore off. He got the ego boost, the chase, and the validation. The second it shifted from spontaneous fantasy to real-world responsibility, he bailed. That’s not mystery that’s male predictability at its most basic.

    You didn’t “do something wrong.” You just assumed intensity equals intention. It doesn’t. He liked the moment, not the implications. Once sobriety, workplace dynamics, and potential consequences kicked in, he did the only thing men who lack backbone always do: he hid. Ignoring you is his cleanup strategy. Not because you were drunk, not because interns saw, not because he’s suddenly noble because he cares more about avoiding complications than he does about you.

    Don’t text him. Don’t chase. Don’t ask what happened. At work, you look him in the eye, give him a neutral “hey,” and move on like he’s a background extra. The second you hint at hurt feelings, confusion, or nostalgia, you hand him power he absolutely doesn’t deserve. He already showed you exactly where you rank in his priority list somewhere beneath convenience and above accountability.

    #49918
    Natalie Noah
    Member #382,516

    The attraction was real but his intentions were short-term. Everything he did in the beginning had heat behind it: the flirting, the late-night messages, the bold kiss in the yard, the chemistry in the truck… that was all genuine. But real attraction does not automatically equal real intentions. From the way he pushed for something sexual right away, from the 2 a.m. meetup to the “explore the tension” comments, he showed you exactly what he was looking for something exciting, physical, and temporary. He wasn’t planning a future with you. He was feeding a moment.

    When guys get what they want emotionally or physically too fast, the chase ends and so does the effort. You didn’t “do anything wrong,” but you gave him a level of emotional access (wanting him to protect you, wanting to see him again immediately, messaging often) and physical access (making out, intense intimacy) before he actually earned that space in your life. To a man who’s not looking for commitment, that kills the chase instantly. He already knows he could have you so he no longer needs to pursue you. It’s not about you being “too much” or “not enough.” It’s about him only wanting the thrill, not the relationship.

    His silence afterward is his answer even if it feels cruel. When a guy goes from texting nonstop to disappearing for days, that’s a deliberate emotional retreat. If he cared, he would reach out. He wouldn’t ignore you, avoid you at work, or go from heated messages to nothing. That switch doesn’t happen when a man wants more. It happens when he’s already gotten the excitement he wanted… and doesn’t want the responsibility or connection that follows. And yes the fact that you’re an intern and he’s technically your superior absolutely made him panic. The moment coworkers knew? He probably freaked out even more.

    If you chase, message again, confront him, ask what went wrong, or act hurt you will only reinforce his belief that this was just a fun fling for him and a deeper emotional hope for you. Men like him pull away faster when a woman tries to figure them out. The most powerful thing you can do now is hold your head high, act calm and casual at work, greet him politely, and live your life. Let him see that he does not get to play with your emotions and walk away unchallenged. Distance is your dignity.

    You didn’t ruin anything. You didn’t scare him away. You didn’t make a mistake. You simply met a guy who was in it for the excitement, the ego boost, the physical spark not the relationship. And it’s better you learned that now instead of falling deeper. Let this be a lesson, not a heartbreak. Next time, let a man show you consistency before you give him intimacy. Let him prove he’s serious before you offer access to your heart.

    #49997
    Sally
    Member #382,674

    You didn’t do anything “wrong.” You were tipsy, you liked him, he clearly liked you, and you both acted on it. That part was mutual. What’s happening now is about him, not you.

    Here’s the real part nobody tells you: some guys chase hard in private and vanish the second real life shows up. The minute he had time to think about it the power dynamic, the fact that co-workers saw, the whole “boss kissing an intern at 2 a.m.” thing he probably panicked. Not because he didn’t enjoy it, but because it suddenly got real.

    He didn’t stop texting because of anything you did that night. He stopped because he realized the situation has consequences, and avoiding you is easier than being honest.

    So what do you do now? Keep it simple. When you see him at work, just be normal. A quick hi, nothing heavy, nothing emotional. Don’t bring up the kissing. Don’t try to joke about him ignoring you. Just act like someone who’s fine and busy and not hanging on this.

    If he wants to circle back, he will. And if he doesn’t, you’ll be glad you kept your dignity instead of chasing someone who suddenly got scared of the mess he helped create.

    You’re not crazy it really was a spark. He’s just not handling it well.

    #54744
    Athena Sky
    Member #382,872

    It’s not a good idea for a woman to chase a man—it can become a turn-off for men because it removes the challenge they’re looking for. My advice is just wait and see if he initiates again. And if he invites you out again, it would be good to clarify what he really wants and what his intentions are toward you, so next time you won’t be confused anymore.

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