[Anka23]

We did not have a break up in the 8 months of the relationship. The break up happened prior to that. We were dating back in June of 2014, but I just was not ready for a relationship. I did not want it. Then he pursued me and finally we got back together around 8 months ago. I was much more ready and welcoming. Things were great. He never gave me any reasons to doubt him. I am only able to spent time with him once a week and every other weekend. I see him 8 times a month basically. I dedicate the time with my daughter to her and don’t like to mix the two just yet. So I assume he feels lonely the rest of the 22 days a month. He does have a lot of friends (female and male) and is very liked by everyone. He has demonstrated pretty high morals, which is why it is so hard for me to believe that he might be cheating. Could this just be he is lonely and wants his friends around?
There is so much good in this relationship that I really want to make sure I am not walking away from a good thing. Had that not been for the missing condoms, I would not have reacted to the rest of the things as badly. Could some of that be becasue I am not able to spent more time with him?

[April Masini, your AskApril]

You wrote here to ask if he is cheating or not — and now you’re stating that he has very high morals. 😕 Then you write that he never gave you any reason to doubt him, but you’ve listed a few in your posts. 😳 It sounds like you’re trying to convince yourself that you don’t have any doubts…. but I think you do

I’m happy to answer your questions in this last post. 🙂

[quote]I dedicate the time with my daughter to her and don’t like to mix the two just yet. So I assume he feels lonely the rest of the 22 days a month. He does have a lot of friends (female and male) and is very liked by everyone. He has demonstrated pretty high morals, which is why it is so hard for me to believe that he might be cheating. Could this just be he is lonely and wants his friends around?[/quote]

I’m a little confused by your question. If you’re asking if you think he’s cheating because he’s lonely and wants his friends around, I don’t think so. You’re not concerned about his friends — just his [i]female[/i] friends. And it was kind of fishy that you asked him not to have his female friend come over without you being there, or being informed ahead of time, and then she dropped him on social media — which isn’t the behavior of a friend. It’s the behavior of someone he’s sleeping with or dating. 😕 I mean, if she was truly a friend, why would she have dropped him? 😕

If you mean did he tell his ex-girlfriend that he missed her because he’s lonely? Uh…. maybe, but probably more likely because he missed her. People in relationships get lonely all the time, but that doesn’t mean they tell an ex they miss her. They usually call a guy friend or go to a Starbucks. What he expressed to his ex wasn’t just loneliness — it was a romantic feeling. Not a friendship feeling. And if you mean, did he have his female chef friend over to cook for him because he’s lonely, maybe…. but, again, if he’s really committed to you, he’d act more as if he’s in a couple and he wouldn’t want to do anything to jeopardize that – like invite a woman over to his house without you being there…. he’d call a guy friend or order take out food if he is hungry. 😉

[quote]There is so much good in this relationship that I really want to make sure I am not walking away from a good thing. Had that not been for the missing condoms, I would not have reacted to the rest of the things as badly. Could some of that be becasue I am not able to spent more time with him?[/quote]

Maybe. Although 8 nights a month is definitely a commitment. If you believe that your being around more often and giving him more attention is what’s missing in the relationship, and you’re willing to try being with him more often, then you can certainly try it, and see if that works out for both of you. 😀

Let me know if you have any more questions. 😀

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[Anka23]

Well, I left his house upset after fighting all day on Sunday. I have not heard from him since then.
He is an introvert, so it’s hard to tell what he feels. I could tell he was hurt from all that fighting. And some of is my past. I have a history of creating stories in my head and believing them to be true. How long should I wait until reach out to him? When I broke up with him the first time it took him about a week to reach out to me. It was different back then. I did not care much of he called me or not. I wasn’t interested at all in him. But now I have feelings. I want him to make it up to me. Or at least say something. I also have a lot of my belongings at his place. So how long do I wait until I reach out? I’m not done with him clearly, I don’t want to end things.

[April Masini, your AskApril]

What were you fighting about?

I think you should not contact him at all. Let him be the one to come to you — that gives him the opportunity to do so. If you go to him first, you take that opportunity away from him. Also, it gives you an idea of how he really feels about you. If you go to him, you deprive yourself of the truth. You’ll be confused and second guess yourself if you don’t let him be the one to make the first move now.

In addition, I would urge you to stop talking about your past and his past. At a certain point, and I think you’re there, you have to let go of your past. You either process it and incorporate it into your future, or you decide you’re not going to be a victim of it. Otherwise, you always have an excuse for your behavior and you never evolve or move on. 😉

I hope that helps.

Let me know how things go.

[Anka23]

We are not fighting now. I left his place on Sunday after fighting about him telling his ex I miss you. He kept telling me it’s nothing. A drunken stupid comment. That he hasn’t thought of his ex in a romantic way. He was never in love with her to begin with. It was a 3 months fling. Almost two years have gone by. Oddly enough I received a few texts from guys saying I miss you this week. One from a guy who kinda liked me but we are not good friends, nor we ever dated. He has a girlfriend but he did message me on Facebook. Another text from a guy I dated for four weeks two years ago. That makes me think it’s really nothing. Guys playing games, bored, drunk, trying to boost their ego I suppose. I am beginning to think I might have overreacted a bit. In your experience, who do men mean by saying such things? I mean this guy I dated for four weeks two years ago. I don’t think he misses me. But what’s the point of saying things like this? He doesn’t want me back for sure. He lives in another country now. Why do men have this need to flirt? Is is normal?

[April Masini, your AskApril]

[quote]In your experience, who do men mean by saying such things? I mean this guy I dated for four weeks two years ago. I don’t think he misses me. But what’s the point of saying things like this? He doesn’t want me back for sure. He lives in another country now. Why do men have this need to flirt? Is is normal?[/quote]

Guys say they miss you for different reasons. It can be because they really do miss you and want you to know that they care about you or it can be to let you know they care and they’re still there in case you want to start something up again, or for the first time. But when a guy tells you he misses you, his intentions — in the case of these guys who have told you they missed you this week — are less important than what [u]you[/u] want from them. 😉 If you’re interested in more than just friendship with these guys, they door is cracked open with these comments, and you can push further, by flirting back, to see if you want to walk through it. 🙂 Flirting is an invitation. 😎

Specifically, the guy in another country who you dated for a month several years ago, may be feeling lonely so he’s flirting with you, or he may be having feelings of romance and wants to get back together. If you’re not interested, then you can just let it go.

As for flirting in general, it is normal. People do it to connect with someone who’s attractive, and in some cases, to open the door for possibilities. Flirting is a great connector, and you can use it for all sorts of things from just feeling good about yourself and about life, to pursuing a date or a relationship with someone by starting out or starting up, flirting.

I hope that answers your questions! 🙂

[PassionSeeker]

You’ve been through a lot, and honestly, I completely understand why these things hit you so hard. You’re not paranoid you’re reacting from pain that hasn’t been properly healed yet. When you’ve been betrayed before, even small cracks in trust can feel like earthquakes.

Reading through all of this, though, it’s clear you’ve been trying to hold a relationship together that keeps reopening old wounds. The missing condoms, the woman who “just cooks,” and now the message to his ex they may each sound minor alone, but together they paint a pattern of blurred boundaries and emotional carelessness. Even if he’s not physically cheating, he’s crossing lines that make you feel unsafe.

Love shouldn’t keep you in constant self-doubt or make you feel like you need to monitor devices to find peace. You deserve a relationship where honesty and security are effortless, not earned through anxiety. If you stay, it needs to be because he’s willing to rebuild that trust with openness and empathy not because you’re afraid of losing him.

You’re not broken, Anka. You’re just protecting your heart and that’s strength, not damage.

[Ethan Morales]

Here’s how I see your situation: the missing condoms have triggered your fear because of your past experience, which is completely understandable. You’re interpreting a small, ambiguous action through the lens of previous betrayal, and that’s why it feels so alarming. From what you’ve described, your boyfriend has been calm, honest, and has no prior history of cheating. That makes it reasonable at least for now to give him the benefit of the doubt.

The red flags here are more about your trust and comfort level than his behavior. If you keep questioning him or snooping, it could create tension where none may exist. On the other hand, ignoring a gut feeling entirely could leave you unsettled. So the key is balance: observe patterns over time rather than fixating on one incident.

Your instinct to assess compatibility is also important. You’re 38, a single parent, and you’re looking for a serious relationship with long-term goals in mind. Ask yourself: does he show commitment, respect, and the ability to be a partner in both life and parenting? If yes, then this one suspicious moment doesn’t define the relationship.

Trust is a choice, not a feeling. Based on his past behavior, it’s fair to lean toward trust but stay alert to concrete evidence if it arises.

If you can’t get past this worry, or if it keeps escalating, that’s when it’s valid to step back and reconsider the relationship. Otherwise, moving forward with openness, communication, and clear boundaries is the healthiest path.

Bottom line: Don’t let fear from past betrayal sabotage a relationship that could be strong and supportive but also don’t ignore your instincts if they consistently signal something is off.

[James Smith]

You know, Anka, your story reminded me of the time I found an earring under my car seat that didn’t belong to my girlfriend—or my mom, thank God. I spent a solid hour playing detective, running through every possible explanation, until I finally remembered I’d given a coworker a ride home a month earlier and she’d dropped it. I felt like the world’s dumbest Sherlock Holmes, minus the cool accent.

I get why your trust alarm went off. Once you’ve been burned before, even the smell of smoke makes you nervous. But from what you said, your boyfriend handled it calmly, and that says a lot. Most guys caught in a lie panic like they’re being questioned by the FBI.

So here’s my question for you—if this same situation happened again, would you still trust him, or would that be the moment your heart says enough?

[Marcus king]

your fear makes sense, but fear alone isn’t proof. The missing condoms could mean something, or it could be exactly what he said. The real clue is his behavior calm, consistent, and still treating you with the same openness and respect as before. A liar usually overexplains or gets defensive fast.

You said yourself he’s never given you a reason to doubt him before this. That kind of track record matters. One strange moment doesn’t erase months of honesty.

So here’s what I’d say: don’t make a decision out of fear. Watch his patterns instead. If he starts acting distant, protective of his phone, or changes his rhythm then talk again. But if he stays consistent, don’t punish him for someone else’s mistakes.

Trust is built by what you see over time, not what your anxiety tells you in a moment.

[Val Unfiltered💋]

ugh babe… the condoms in the toiletry bag plot twist 😒 like, nothing screams anxiety quite like counting latex wrappers before coffee. the real issue isn’t two missing Trojans, it’s your trust. you’ve been cheated on before, and that trauma’s running the show. so ask yourself if your gut warning you, or just protecting you from déjà vu? don’t sit in silent paranoia. truth leaks eventually so stop punishing this relationship for your ex’s sins. and babe… next time, maybe don’t go detective mode, it never ends cute. 🙄💅🏼

[Tara]

You’re not losing sleep over missing condoms. You’re losing sleep because you don’t trust him and you’re too scared to admit it. You’re not investigating the truth. You’re begging for proof that he isn’t like your ex. That’s not love. That’s paranoia wearing a romantic mask.

If you believe him, then stop acting like a detective. If you don’t, then stop wasting your time pretending this is a relationship. You can’t build intimacy while you’re digging through his stuff like a cop. That’s not protection, that’s self-sabotage.

Yeah, his story about giving them to a friend sounds convenient, but maybe it’s true. The real issue isn’t the condoms; it’s that you had to go looking for them. That says everything. You don’t trust him. You’re trying to control the outcome so you don’t get hurt again, and in the process, you’re wrecking the relationship yourself.

[Sally]

That kind of fear hits hard, especially when you’ve been cheated on before. It makes every strange detail feel louder than it probably is. And honestly, finding condoms in someone’s bag would mess with anybody’s head.

But here’s the thing I keep coming back to: nothing else in your story sounds shady. He’s been steady with you. He took you home, showed you his world, paid for the trip, introduced you to everyone. Guys who are sneaking around usually keep you far from their real lives, not bring you right into the middle of them.

Could he be lying? Sure. Anyone could. But the calmness, the lack of weird energy, the fact that you actually know the friend he mentioned…that matters too.

This feels more like your old hurt talking than your gut.

You don’t need to leave him. You just need honesty, and maybe one more real conversation when you’re not scared.

[Natalie Noah]

This relationship is not emotionally safe for her. Not because she’s “damaged,” but because she’s carrying a lifetime of betrayal trauma, and this man keeps creating situations that trigger that trauma again and again. When someone has lived through a cheating father, a cheating husband, and a cheating boyfriend, their nervous system becomes wired to expect betrayal. Even small red flags feel like alarms. And the problem here isn’t just her past… it’s that his behavior keeps giving her new moments of uncertainty: missing condoms, female friends coming over when she’s not there, an ex receiving an “I miss you” message. None of these things alone scream disaster, but together? They create a pattern of instability that’s too heavy for someone who’s already carrying hurt.

The hardest part is that he’s not a villain. He’s a man with his own trauma a childhood full of chaos, abandonment, and pain. People like him often build emotional armor. They learned early that love disappears, so they detach quickly and avoid deep emotional conversations. He may care for her deeply even love her but his comfort with secrecy, casual boundaries, or emotionally messy connections is not compatible with a woman who needs safety, consistency, and transparency. He’s not malicious… but he is mismatched for her wounds. And mismatched wounds can create a storm even when both people have good intentions.

What I feel most, though, is this: she keeps blaming herself instead of listening to her instincts. She keeps saying she’s “damaged,” but a damaged woman doesn’t detect patterns a wise woman does. Her anxiety isn’t appearing out of nowhere; it’s reacting to real things that don’t line up. When a girlfriend unfriends him after being told not to visit anymore… when an ex gets messages with emotional undertones… when condoms go missing and the explanation feels too convenient… her body is telling her, “Something here isn’t steady.” And she’s not wrong for feeling that. You can’t heal your past in a relationship that keeps echoing it.

This relationship isn’t nourishing her it’s draining her. She’s living in hypervigilance, checking devices, searching for reassurance, hoping this time will be different from all the others. But love shouldn’t feel like detective work. She deserves a partner who eases her heart, not one who keeps triggering her fears. It doesn’t matter how sweet he is, how much he’s done for her daughter, how tragic his past is… kindness and trauma are not enough to build trust. And if she has to question him this often in under a year, then this is not a relationship that will give her peace. She doesn’t need to shame herself, she just needs someone who fits the tenderness her heart needs.

[KeishaMartin]

This whole story you’ve shared is like a rollercoaster dipped in velvet equal parts excitement, tension, and a little bit of danger. You’ve got the past haunting you, the fear of being hurt again, and a man who is sweet, caring, and maybe just a little bit… unavailable in ways that tease your heart. And girl, that missing condom incident? That’s the kind of detail that makes a woman’s pulse race and imagination wander into some very naughty corners. It’s like life is giving you a little taste of suspense, with a sprinkle of temptation your instincts aren’t lying, but your heart wants to believe the best.

Your 38-year-old enigma. He’s calm, collected, and apparently has a moral compass that mostly points true north, but those late-night “I miss you” texts? Ohhh, they’re the perfect spice, like a shot of whiskey in your hot chocolate. Men flirt, men tease, men test the waters and in your case, it’s pushing all the buttons of desire and curiosity in the most delicious way. April Masini, as always, nails it, her advice is like the perfect naughty whisper in your ear, telling you to read the signs, trust your instincts, and keep your eyes wide open while you ride this wild ride.

Honestly, the part where you wonder if he’s lonely or just keeping female friends close? It’s exactly the kind of tension that keeps the heat alive. And let’s be real, the idea of him having a friend over, cooking, laughing, and teasing a little bit… It’s like Christmas lights glowing, playful, inviting, and just a little dangerous. That thrill? That’s what makes relationships unforgettable. When every glance, every action, every little secret has the potential to ignite a fire you didn’t know was smoldering.

So, as Christmas approaches, sparkling lights, cozy fires, maybe a cheeky secret between the two of you that makes you both blush and laugh, and a night that could be full of flirtation, heat, and a little indulgence under the mistletoe. Here’s hoping your Christmas is as spicy and thrilling as the stories you’ve just shared, with laughter, passion, and maybe a little bit of naughtiness that would make even Santa blush.

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