Navigating the Emotional Rollercoaster of Dating: Lessons from a String of Tough Relationships

[rayzoredge]

So, here’s the thing: I’m stuck in this weird place where I simultaneously despise the idea of a relationship and desperately want one. It’s exhausting. Let me break down how I got here.

My Track Record

First girlfriend – end of junior year, band geek. She’d been crushing on another guy for months, asked me for advice, then suddenly liked me. I was so thrilled someone wanted me that I ignored the red flags (she’d dated half the band). It fizzled out when I moved schools – mutual drift.

Second – almost a pity thing. She approached me, but it was all about her: trophy girlfriend, no real connection. I ended it after a hissy fit.

Third – introduced by the second. She was legitimately mentally unwell – believed in past lives, thought she was a cat, self-harmed, cheated on me with my best friend. Twice. I forgave the first time, but the second? Peace out.

Fourth – friend of the third, crush on me. She started copying the third’s bizarre behavior. I was about to break up when I accidentally kissed her friend (who became the fifth). Messy.

Fifth – that friend. We were great for a month, then I left for basic training. She broke up via letter before Christmas. Later found out she was dating an “old friend.”

Sixth – met online. Spent six months talking daily, webcams, intense. Flew to meet her. She threw a party, got drunk, and I woke up to her having sex with a stranger. I walked out at 4AM.

Seventh – my best friend’s younger sister (17, I was 20). She wanted a relationship, I hesitated. Friends-with-benefits became a thing. After she lost her virginity to me, she said I was too old. Days later, she was with two other guys. I told her dad out of concern – disaster. She cut me off.

The Result

I’m bitter. Cynical. I can’t look at a woman without thinking she’ll use me or play games. Even my good intentions blow up. I want someone, but I’m terrified of hurting them or getting hurt. The shyness doesn’t help – I never make the first move. When I finally did (asked out a German girl at a bar), she said “Nein, nein, nein” because her ex was at the next table. Talk about timing.

I don’t know how to break this cycle. I’m tired of feeling like this. Any advice from people who’ve been through similar?

[References]

Topic Overview (Wikipedia):

Relationship most often refers to:Family relations and relatives
consanguinity
Interpersonal relationship, a strong, deep, or close association or acquaintance between two or more people
Intimate relationship, close relationship that may involve feelings of romance or love and sexual intimacy
Correlation and dependence, relationships in mathematics and statistics between two variables or sets of data
Semantic relationship, an ontology component
Romance (love), a connection between two people driven by love and/or sexual attraction
— Read more on Wikipedia

YouTube Video:

Healing After Heartbreak 💔

[TikiPrincess]

I appreciate you being this open. It takes guts. But reading through, I noticed something: every story is from your perspective, and you’ve painted yourself as the victim in most of them. I’m not saying those girls were perfect – far from it. But relationships are a two-way street, and it’s worth looking at your own patterns.

Some Hard Truths

1. The band “cheerleader” – you ignored obvious red flags because you were flattered. That’s on you. Learn to vet people before diving in.

2. Dating friends of exes – huge red flag. Girls (and guys) often have competitive friendships. You become a trophy. Walk away.

3. Long-distance military relationship – incredibly hard. She probably had her own fears (you might not come back). The letter-writing issue? Maybe she needed more emotional warmth. Not excusing cheating, but communication gaps matter.

4. Online dating – especially sites like MySpace (which is basically a black book). Flying to meet someone after six months of intense online interaction? You built a fantasy. Real life rarely matches. She was probably nervous too – doesn’t excuse what she did, but you put yourself in a volatile situation.

5. The virginity situation – taking someone’s virginity is a huge deal emotionally. She likely felt confused and vulnerable. Instead of comforting her, you told her dad. Even if your motives were good, that was a betrayal of trust. She pushed you away because she didn’t know how to handle the intensity.

What Now?

Stop waiting for girls to approach you. Decide what you want from a relationship – not a checklist of traits, but values: how you want to spend time, how you handle conflict, what intimacy means to you. Then go out (real life, not online) and interact with people without the pressure of dating. Build friendships first.

And for the love of everything, work on your shyness. It’s not attractive to be passive. Confidence comes from action, even if you fail. That rejection at the bar? That’s just life. You’ll survive.

You’re not doomed. But you have to own your part in these messes. Reflect. Grow. Try again – but smarter this time.

[rayzoredge]

You’ve gotten some solid honesty from TikiPrincess, and I think that’s exactly what you need. I’ve been in a similar loop—dating people who were either unavailable or just plain wrong for me, then wondering why I felt hollow afterward.

One thing that stood out in your story: almost every relationship started because someone else approached you. First girlfriend, second, third, fourth, fifth—they all made the first move. That’s not necessarily a bad thing, but it does mean you’ve been reacting instead of choosing. And when you’re not actively selecting who you invest in, you end up with whoever happens to want you at the moment—which is rarely the person who’s actually good for you.

The shyness piece is real. But the fix isn’t just “be more confident.” It’s about figuring out why you’re so afraid of rejection that you’d rather let others decide your love life. That German bar moment? It wasn’t just bad timing—it was you finally stepping forward, and it didn’t work out. That hurt, but it’s no different than any of the failed relationships you already survived.

If you haven’t already, look into the concept of anxious attachment—there’s this YouTube video about Healing After Heartbreak that explains how we repeat patterns until we address the underlying wounds. Also, the Wikipedia article on Relationships covers the difference between surface compatibility and deeper values. Might help you stop treating dating like a lottery and start treating it like a skill.

You’re not broken. You’re just still learning what you actually want instead of what you’ll settle for. That takes time and a lot of awkward conversations with yourself. Keep going.