She just ended an LTR. How long before I can ask her out?

MythicalMagicMan asks: 

I have known this girl for a little over 5 years. When I first met her I was the shy nice guy and I had never been in a relationship before but I expressed feelings for her. At the time she used the whole “I don’t want to ruin our friendship line”. A year later she expresses that she has feelings for me too. She’d come over and we’d get fairly intimate, but never had sex because of my own insecurities. She eventually starts dating another guy so I basically cut ties and reassess my naivety and where I went wrong. I’ve been in 2 relationships since and ended up terminating those myself because they just didn’t work.

So fast forward to now, she just ended a 2 and a half-year relationship with a single father psychopath. They were engaged even though the moron bought them matching tattoos instead of a ring. Lo and behold she starts talking to me again, obviously looking for validation. I’ve learned from my mistakes and understand how not to be the “nice guy”, and what a relationship actually involves. So I let her initiate most conversation and try to keep my distance. She drunkenly dropped the L word in a text as well. I had written this girl off and never expected to see her again, but I always have found it really easy to talk to her, and enjoy spending time with her. I would like to make a move when the time is right.

So, how long should I wait if I can tell she still has feelings for me?

Demetrius says:

Normally, I’d advise a bit of a delay but in your case, you really should just get this out-of-the-way as soon as possible.  She already knows you have feelings for her, she’s known it for five years at this point. You clearly have a certain level of chemistry and connection with each other based on your history. If you guys hadn’t already established a mutual attraction, or didn’t know each other for so long, I’d tell you to put off telling her but man, you’ve waited five years for this moment. It is time to make your move, if you really want to make this move. You potentially risk overwhelming her now while she’s dealing with her breakup, but it’s not like any of this is going to be a surprise to her. So go for it as soon as possible, if you think it’s the right move.

The thing is, I don’t think pursuing her is the right move. She didn’t just break up with a boyfriend, she broke up with a “psychopath” who she was engaged to! Assuming the guy isn’t actually a psychopath and is just kind of a dick, she was still engaged to someone who must have treated her very poorly or was unstable if you’re calling him a psychopath . I understand that some people don’t see red flags but dude, there are red flags everywhere in your situation. If you’re not sure what those red flags are,  let’s lay out your scenario:

  • You’ve previously been physical, but not sexual with this girl. You did not have sex because of your insecurities
  • When she found a boyfriend, you cut ties with her
  • She dated a man you describe as a “psychopath“, then they became engaged
  • She has reached out to you for “validation”
  • Over text and over the phone, she drunkenly told you she loves you

I’m gonna be honest with you, I don’t care if she is the most attractive, charismatic, coolest, smartest, funniest woman in the world, I would not pursue her at all. This all sounds like a recipe for disaster. Not just on her part, but on your part as well.  For starters, you described your own intimacy issues and insecurities, which at no point did you mention that you’ve overcome. You also cut off a friendship with her once she got with her ex, which to me says you can’t have healthy relationships with women unless a) they are related to you or b) they want to be your girlfriend. Maybe that has changed over the last 5 years, but both of those things sound like red flags to me. Who knows, maybe you’re both the perfect level of screwed up to make it work, or maybe you’re both young and figuring yourselves out. Whatever the case, I’d be wary if I was dealing with these issues, but hey, I could be wrong and I’m just speaking from my experience as a 30-year-old guy.

For her part she’s not only going through a breakup, but also the end of an engagement. That’s a huge deal! People deal with breakups differently of course and it’s possible that you wont just be a rebound guy. But I’d be wary of dating a girl who was reaching out to men for “validation”, whether it was during or after her last relationship. That just seems like really suspect behavior to me if she did it while she was with her ex. If she did it after she broke up with him, it’s the behavior of someone who lacks confidence and requires validation for men to determine her self-worth. Either way, I’d NEVER want to date that girl. I am sorry if that seems harsh, but I’ve dated that girl in the past and it never, ever ends well.

In summary, if you really want to pursue her again, now is the right time to let her know how you (still) feel. If I were in your shoes, I wouldn’t pursue her at all, because quite honestly I doubt dating her could end well.

Good Luck Out There.

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