Dear Breakup Girl,

This is kind of a biggie. I’m 23 years old. I still live at home with my ‘rents for financial reasons while I’m in graduate school, completing a degree in elementary education.

To get down to it, I haven’t had a date since I was 17. It’s not for want of trying. The times when I thought there was some mutual attraction, I would ask to see the person more socially, not necessarily on a date, but out. The few times that anyone has said yes over the past 6 years, it’s always turned out they were just being friendly, but were already involved with someone else. Plus, I suppose I’m not that good at reading “signals.” That takes experience, something I am greatly lacking.

Most of my friends are women, but I’ve never been able to move a friendship to a romance, nor have I really tried. I would consider it almost a betrayal of that friendship. I’m not into the bar scene, or clubs (I can’t dance). I’m not into religion, so meeting someone at church is out. I’ve tried personals, both online and off, with 0 success. For all that my best friends are women, none of them has ever set me up with someone.

Now it seems that all my friends are engaged, or involved in serious relationships (and as a consequence have little if any time to spend with me). My little sister, and my best friend’s little sister (same age, 3 years younger) are engaged. And every attractive, intelligent woman I meet seems to be married/engaged/or otherwise seriously involved. (I’m only meeting people at school and work. I hate going out by myself, and never meet anyone when I do.)

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Straight to the point on August 31, 1998…

Dear Breakup Girl,

I am seeing a guy who is older than me. He can go to bars and clubs and I can’t. Do you have any ideas on good dates that he would enjoy?

— PA Girl

Dear PA,

Yeah, I got a million (sports games, sports activities, going to movies, renting movies, eating out, baking cookies, etc.).

Does he?

Just making sure that when it comes to fun, you’re not doing all the work.

Love,
Breakup Girl

MSN.com, Match.com, HappenMagazine.com: they’re in a healthy and satisfying 3-way relationship. Meaning that you can find MSN/Match.com’s “Ask Lynn” columns –penned by BG’s alter ego — over at Happen now as well.

This week Lynn hears from Stressed Jess who’s getting back out there after a finally ditching a “stuck” relationship.

The only problem is that my town is a small conservative town where there aren’t a lot of options. I’ve tried the whole online dating thing, but some people are just too far away or some just seem to want a fling. … How do I get back into the dating world?

Read Lynn’s advice at Happen, then come back here and add your own suggestions below!

Making acquaintances on July 13, 1998…

Dear Breakup Girl,

Okay, here’s my situation: I’m a 24 year old male who moved away from my friends and family to attend a University. This college town has been my residence for the past six months; this is my first time away from home. Life is great for the most part except for one minor inconvenience: I don’t have a girlfriend or more importantly, friends.

Before I moved up here, I was surrounded by my tight group of cronies. I’ve even been fortunate enough to have a few relationships with some righteous babes. Now that I’m living on my own, I find it difficult to make friends. At school, there’s a few acquaintances that I sometimes chat with but I really don’t have a whole lot in common with them. So the chance of me hanging out with them is pretty slim. It seems like whenever I’m in a social situation I tend to clam up and make people think that I’m some kind of snobby bastard. In reality I’m actually a decent-looking, nice guy (no really, I am) so I’m not sure what my problem is.

Around town, I’ve seen a lot of local goddesses that I’m quite attracted to. It’s really not my style to go up to them and say, “Hey baby, if we were an alphabet I would put U and I next to each other.” All my relationships in the past have been initiated by her, meaning I have never played the part of the aggressor. Keep in mind that I have never been in love before and I’m beginning to think that I never will.

I have worked extremely hard to become independent and start my new life in this college town. There is no way in hell that I’m gonna move back home because of my loneliness. I’m not sure how much longer I can live without having any friends to drink beer with or any girls to snuggle with. I love being alone but I hate being lonely. Boy am I a mess.

–Dateless and Lonely

BG’s righteous answer after the jump!

MSN.com, Match.com, HappenMagazine.com: they’re in a healthy and satisfying 3-way relationship. Meaning that you can find MSN/Match.com’s “Ask Lynn” columns –penned by BG’s alter ego — over at Happen now as well.

This week Lynn gets pulled over by Sgt. Frustrated, a female cop who’s having trouble detaining the opposite sex…

I’m middle-aged, divorced, in great shape and look young. I also have a very good job and am squared away financially — all pluses. … So, what’s the problem? My career is in law enforcement. And more frequently than I like, potential dates back away from that.

Should this officer even bother with gentlemen who are intimidated by her? Is there something she could be doing differently? Read the full letter and Lynn’s advice at Happen, then comment below!

Related: Breakup Girl’s European Vacation!

About finding a boy on April 20, 1998…

Dear Breakup Girl,

What is the consensus about men dating single moms? I am an educated, attractive, fun to be with, early 20’s woman with a 7-month-old son. I broke up with his father about two months ago, but lost interest in the father about five to six months prior. I would like to meet someone, but am scared no one will want to date me because of my baby. Where would I meet a guy?

— Single Mom

Dear Single,

Yeah, it might be a little tricky. Everyone — male or female — who fantasizes about having all sorts of firsts with their soulmate might think, “No fair, s/he already got to do the kid thing with someone.”

Still, it can be done. I checked with my single mom friend Rachel — who, mind you, is getting remarried shortly! — and she says you definintely want to be discreet (but not cagey) at first. “I asked a guy to come into Toys R Us with me, and I never heard from him again,” she says. But she also pointed out that you do have a built-in screening process: it’s not that a guy for whom a kid is a deal-breaker is bad — but the ones who do stick around are, more than likely, way into you, and not freaked about the dad thing.

But where? By this point, Rachel’s 14-year-old daughter piped up. “Parent-teacher conferences!” Not a bad idea. But I bet you’ll find someone before your son is old enough to give advice.

Love,
Breakup Girl

Dating expert Rachel Greenwald made a splash with her 2003 self-help book Find a Husband After 35: (Using What I Learned at Harvard Business School)and spent years researching her 2009 follow-up, Why He Didn’t Call You Back: 1,000 Guys Reveal What They Really Thought About You After Your Date(re-christened for its March 2010 paperback release as the more empowering and less finger-waggy Have Him at Hello: Confessions from 1,000 Guys About What Makes Them Fall in Love . . . Or Never Call Back) by interviewing 1,000 men about their honest reactions to real dates.

Through the insights gleaned from these candid chats, Greenwald, a professional yenta and dating coach, became a staunch advocate of third-party “exit interviews” for both men and women who have been blown off after one or two dates and desire some useful info about what might have gone wrong. She likens these post-mortems to performance reviews at work, and thinks they are the key to discovering potentially stymieng blind spots about one’s own dating behavior. Recently Greenwald has begun training others to become professional “exit interviewers.” Here’s what she had to say in an INTERVIEWinterview with BreakupGirl.net:

Why do you think it’s helpful to know why someone didn’t call you back, as opposed to just letting go and moving on?

Rachel Greenwald: Well, it’s like anything in life. Feedback improves your performance going forward. It’s a tool. You could be doing something like sending the wrong signal, or giving the wrong impression, and…not getting the results that you want. If only someone could coach you about how you were perceived and what went wrong, you could use that information to change things and get better results next time.

Do you think most people being “exit interviewed” are going to be honest?

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Via BuzzFeed. (More here.)