[Anonymous]

ok i’ll try to make this short and to the point but i can’t make any guarantees 😉 …

last summer/fall i met this guy — we went out for about a month but it didn’t really go anywhere…until recently. a few (maybe 3 weeks ago?) i got this random 2 am text from him…”hope you’re doing well blah blah blah let’s grab a beer sometime.” first thought was that he was a d-bag who couldn’t score at the bar that night but then i decided to give him the benefit of the doubt and responded the next day. ended up going out with him later that day, had a good time, etc. etc. he kind of gave an explanation for why things didn’t work out between us earlier — off and on relationship with an old girlfriend. no big deal, it definitely made me feel better about things not working out earlier. i mean, i didn’t really feel bad that he’d want to try to work things out with someone he’s known for quite a while as opposed to someone he basically just met. so anyway my bitterness dissolved and i’ve gone out with him relatively frequently since then, but with a super cautious and guarded attitude. basically assuming this is most likely going nowhere and he’s not really interested in anything more than hooking up, i should proceed with caution, have fun and DO NOT get attached.

fast forward to today. we went out last night and had a good time but his phone kept ringing all night and all throughout the night. 3 am, 8 am, you get the idea. i just figured it was drunk friends or something, but while he was in the bathroom i noticed a letter folded in half on his kitchen counter, and i know it was none of my business, but i glanced at it anyway. i definitely didn’t pick it up or unfold it or anything, but i caught a couple lines and basically his ex girlfriend misses him, will always love him, blah blah blah none of my business (i ask for leniency because it was in plain sight 😕 ) didn’t really think much of it but it kind of brought me to reality a little bit. and of course i didn’t follow my own advice and i’m starting to actually think i might be interested in him and that there’s a chance, albeit a small one, that the feeling is mutual.

anyway, she called while we were at breakfast, and without thinking that it could be her, i told him i wouldn’t be offended if he needed to take a call. he said it was a call he didn’t to answer and went on about how she’s been calling a lot, wanting to get back together even though she broke up with him. i masked it well but immediately my girl insecurities kicked in and i was fully thrown back into reality. i kind of got bummed out a little. i figured since he didn’t want to end it with her earlier and i didn’t really stand a chance then, why would i now.

i’m kind of not sure how to proceed with this at this point. i mean, it’s definitely inappropriate for me to ask where things are going and where her and i fit in the picture, especially at this point in our relationship or whatever the appropriate term is and obviously i can’t straight up ask him. but how do i know if it’s just hooking up and not going anywhere substantial or if i’m just bracing for the worst? i think if i knew for certain if he was really past his ex then i’d be able to continue with the cautious attitude i had before and just take it easy. but if there’s a good chance that he’ll just want to work things out with his ex again, wouldn’t i be better off just walking away from this all together and save myself some disappointment and a hint of dignity?

any idea if the cards are stacked against me and i’m just there to pass the time until he patches things up with his ex? or is it ok for me to see him again and let myself be interested in him? thanks for your help! it’s always nice to have someone not involved look at these situations with a clear and unbiased opinion.

[April Masini, your AskApril]

You’re not listening to your own very good instincts! 🙄

A 2 a.m. text is NOT what a man who respects and cares about you sends as a first communication after months of not communicating. Your instinct that he didn’t score at the bar that night, so he’d text you instead, was correct. When you did respond to him the next day, it sounds like you agreed to date him that very day! This is not what I would have recommended at all.

(You NEED my book, Think & Date Like A Man!!! Order it here [url]https://www.askapril.com/relationship-dating-advice/think-and-date-like-a-man.html[/url] and READ it!!)

Your instinct,[i] “basically assuming this is most likely going nowhere and he’s not really interested in anything more than hooking up, i should proceed with caution, have fun and DO NOT get attached. “
[/i] was correct. [b]But you didn’t follow it![/b] 😡 You shouldn’t be dating someone more than once who’s only interested in hooking up with you. It’s not a good dating practice for someone who wants a real boyfriend, let alone Mr. Right.

Now, you’re invested because you’ve had sex with him (sex has a much different effect on women than men, and it tends to bond women to men emotionally in a way that doesn’t work in the opposite direction), and you’re realizing that he’s getting suspicious calls and letters from his ex-girlfriend and maybe others at all hours of the night.

You shouldn’t ask him where you stand in your relationship because he’s given you enough hints and clues for you to figure it out already. You’re in a casual relationship with him. I wouldn’t be surprised if he’s dating or ready to date other women at the same time as you. When you read my book you’ll get ALL the hints and clues to look for, but basically, if a man is serious about you, he’ll introduce you to his friends as his girlfriend, he’ll start acting like he’s in a couple, rather than a single guy, and he’ll have you meet his family because he’s so proud of you, he wants to show you off as his.

I think you have very good instincts, and you’re not following them. You’re going to get a lot out of my book, because it’s going to help you understand how to date and whom to date. Read it! And let me know how things go.

[Anonymous]

thanks april. i appreciate your insight on this, most likely a-typical situation.

i think i’m just a little thrown off because when he wants to get together, aside from the lone 2 am text, he gets in touch with me a couple days ahead and we’ll make plans in advance like normal people. like last weekend he suggested we grab sushi this weekend and that he’d get in touch with me later on this week. i don’t get why he’d go to that kind of trouble if he’s just interested in hooking up. although it probably doesn’t mean much and i’m just trying to justify it in my head.

and not to sound hopeful or pathetic, but generally speaking, do casual relationships ever evolve into something else — friendship, relationship, etc? not necessarily related to this particular situation, i’m just curious in general, although i’m assuming it’s not that often.

thanks again!

[April Masini, your AskApril]

I don’t doubt that he likes you, but I think he may be into his ex-girlfriend, too. Clearly, if he wanted to tell her it’s over and not to call again, he would. But it seems like he’s not giving her the signals that he’s totally uninterested in her. That’s where your “girl instincts,” as you refer to them, kick in.

Casual relationships can DEFINITELY evolve into something deeper and even long lasting. And what I hear is you wanting to proceed in the relationship for now, so if that’s your plan, then do it with caution. Keep your instincts honed, and your eyes and ears open.

I hope that helps for now.

[Anonymous]

thanks april! turns out i wasn’t as into him as i thought i was. plus i think my job kind of clashed with him politically, yet intimidated the hell out of him. good thing i didn’t bring him to an office party! 🙄

speaking of, why is that the case? that certain careers total scare men off? my job is far from glamourous, and definitely not financially rewarding (i work in criminal litigation at the appellate level), but i worked my ass off and made a lot of sacrifices in law school, socially, financially and relationship-wise, which you would expect him to understand considering he’s an attorney as well. sorry maybe that was just me venting. 🙂

[April Masini, your AskApril]

Men like to feel like, well, men! They want to feel like they’re the strong one in the relationship. They want to be the breadwinner — or at least the bigger breadwinner. They want to know they’re the best sex you ever had, and nobody makes you feel like they do.

If you are a stronger woman than he is a man, he’s going to feel “less than” around you. And while you may think that because you don’t have a glamorous or high paying career, there is probably something about your commitment, success and/or ability to handle criminals and criminal litigation that makes him feel less strong than he wants to feel around a woman.

You need a man who is very sure of himself and is confident in his own right so that your career and your confidence don’t make him feel inferior.

[Member]

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