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Dating : Something is holding me back from developing deeper feelings for this guy, but I don’t know if I’m being fair to myself, or if I’m being my own worst enemy?

Dating : Something is holding me back from developing deeper feelings for this guy, but I don’t know if I’m being fair to myself, or if I’m being my own worst enemy?


I’ve [24 F] been seeing this guy [25 M] for about two months now, and have been on about 10 dates. From the start, I’ve always had this kind of mental block holding me back from opening up and developing deeper feelings for him. I think part of it is that I feel most like myself (goofy, comfortable, etc) around him, and it reminds me of how I felt with my ex, so it makes me scared of getting hurt again. I recognize though that feeling like myself and comfortable around him is a great thing. He’s attractive (to me), smart, values mental health/therapy, athletic, the sex is great (he’s the only guy that’s ever made me orgasm from sex alone), and we have a lot of common interests.

But, there are also some things that I don’t know if I like about him or not. He always makes us split the check on dates and sometimes just let’s me pay for the whole thing and never offers to pay me back (please don’t crucify me for saying this–it’s just a personal thing for me–I like it when a guy pays for the bill sometimes and I do NOT have a problem with splitting but sometimes his behavior comes across as cheap?? I also always used to offer to pay for stuff with my ex and sometimes he took advantage of that so I guess that’s why now I look for a guy that is willing to pay for stuff without being asked to). He is pretty messy but that’s not a dealbreaker for me per-say, but it does get annoying when we always spend time at my place and never his because he says its messy. He always gives me compliments but get’s kind of jokey (but he’s kind of serious) when I say thank you and don’t immediately give him a compliment back? Which kind of annoys me sometimes, but again not a dealbreaker.

****NOW THE IMPORTANT BIT..****Here comes the big potential red flags (but I don’t know if I’m overreacting). He spent a full 24+ hours at my place one weekend. Came in the afternoon the day before, and didn’t leave until the next night basically. This was probably like the 7th or 8th time we hung out together. He was supposed to leave in the afternoon after breakfast, but he said he wanted to stay longer to spend more time with me so I said okay and I was actually starting to really open up more. Then he said he had to meet up with some friends around 8pm. We had sex around 7pm (as well as multiple times that day), and he left at 7:30pm to go home and get ready to go to the bar with friends. He told me this elaborate story about his plans with friends that night, and i told him I hope it would be fun. He also had a short talk with me before he left saying that he wasn’t seeing anyone else besides me on dates, and didn’t think we needed to use protection because he wasn’t sleeping with anyone else either. I told him, we weren’t exclusive yet and I think it’s okay if he goes on dates, but he insisted he didn’t want to see anyone else besides me.

Around 8:30pm-9pm ish I go to this restaurant with my friend on study break to pick up takeout, and I see this guy on a date…. I didn’t see any of the friends he said he’d be with…only one girl. It killed me a little because it actually seemed like they were having a great time. And then I wondered if he only stayed at my place longer that day because this restaurant was right next to my apartment. I texted him saying that I thought i saw him but I didn’t want to say hi because he seemed busy, and he didn’t respond to me an hour later, and said if I was still at the restaurant to come hang with them. He then called me and hung up. I called him back 3 times and he didn’t answer until almost midnight. He said he was with a friend and wish I could’ve hung with them and that he just dropped her home. I told him I didn’t believe him and that it was okay if it was a date, I just wish he would be honest. He started to laugh and said « wow I can’t believe you think I’m lying, let me give you a timeline of events!! ». He gave me some bogus timeline of events, saying his friends were there but walked out and he ended up messing up some times, kept laughing at me for thinking he was lying, but I stood my ground and I basically caught him in his fake timeline of events. Then he said his friends set him up on a blind date with his friend from class and left mid way during dinner so him and the girl could hit it off. THEN he changed what he said, he finally admitted it was a girl he didn’t know (she wasn’t his classmate) and his friends set him up but were never there to begin with and that he never made plans for a date and didn’t know where the date would be. I told him it just seemed weird to me that he fucked me 30 mins before this date and decided to go on a date hardly a 10 min walk from where I live. He said he didn’t plan the date to be so close to my apartment, his friends told him to go to this restaurant. **The thing is**, after he said that, I remembered seeing a notification pop up on his phone from a reservation website/text thingy before he left my place, but he had taken his phone quickly and I didn’t see what it said past that so I thought it must’ve been for his hangout with his friends. So I still think he was lying. But, I got hurt because he didn’t need to lie. I told him it was okay for him to go on dates because we aren’t exclusive, but he still lied and kind of gaslit me when I saw him with my own eyes on a date. And I understand why he wouldn’t tell me he was going on a date prior to that, but why lie after the fact after I saw him?

He came to my apt the next day to apologize because he said he wanted to rebuild my trust. He choked up on my couch and said he really wanted to still see me and had wanted to become exclusive soon, and to give him a chance to prove that lying isn’t like him and this was a one time thing. He said he isn’t going on dates with anyone right now. I said okay, and he spent the night, as well as came over the next day. So we basically spent three days in a row together.

**Flash forward a week later**, my best friend messages me about a guy she matched with on a dating app AND ITS THIS GUY. Not only that, HE MESSAGED HER ON THE APP LITERALLY A MINUTE AFTER CALLING ME TO TELL ME HE WAS AT MY APT AND TO LET HIM IN SO HE COULD APOLOGIZE A WEEK PRIOR. Literally, when I checked my call log, he called me to let him into my building, and messaged her on the app 60 seconds later while I was on my way to get him. After he choked up on my couch and everything. I texted him and told him I felt like he was manipulating my feelings and that he kept lying about things he didn’t need to lie about. He told me a month ago he hadn’t used dating apps at all since meeting me, he told me a week prior he wasn’t seeing anyone else. All the while I keep telling him its okay if he wants to because we aren’t exclusive yet. So why lie when you could just not say anything?????

He told me he just uses the app as a confidence booster, and that he only messaged my friend with the intention of never going on a date with her. I told him it doesn’t matter whether he would have gone on a date or not, I guess I was just bothered again about the lying. Then he told me I misheard him and that a month ago, when he told me he hadn’t been using dating apps since meeting me *he had mentioned a specific app*. But I only recall him ever saying ALL dating apps. So now I feel crazy and I’m second guessing what I heard.

I don’t know if I’m overreacting or not, so I’d really like a second opinion. Please be kind, I’m really trying to keep an open mind and not be crazy, because I do feel a little crazy for even being hurt at him. And these events have been keeping me from opening up and falling for him, but I don’t know if these are fair things to hold me back, or if I’m being my own worst enemy and overthinking it? Any advice is really appreciated, because I don’t want to be unfair to this guy. I think I’ve been patient and he told me that he would never have handled this as patiently if the roles were reversed. But, am I overreacting? Or should I be cautious and break it off?

What do you think?

3 Comments

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  1. I don’t think you’re overreacting at all. He has broken the trust and shown red flags, and from what you said in this post the lying would only get worse in a relationship. I think your gut feeling that you should hold back from him is right, and I would say break it off.

  2. He’s totally manipulating and gaslighting you when you’re just begging him to stop and be honest so you can progress. He’s shown he won’t do that so I would be done with him and cut your losses.

  3. He’s an absolute douchecanoe and you should dump him and block him. This is classic narcissist behavior. He’s testing you to see how much he can get away with, and it will only get worse.

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