Sasha, I am 35, never married, no kids. By now, I expected my life to be much more traditional- married with children, and I believe I'd make a great mother. Two years ago, I met R. through work. He's a loner and not interested in most social situations or meeting friends, but we hit it off and have become very close. There was never anything romantic or sexual- we had a "talk" in the beginning with him saying, "look, I want you to be in my life, but if you are hanging around waiting for a relationship with me, you are out of luck. I can barely get my life together at this time, so I'm not the right person to be in a relationship." I wasn't wanting one, and so we moved right along, and stayed friends. It was never romantic-- we always slept in separate beds and we've never so much as held hands. However, our friendship became the most important thing to both of us.

Six months ago, things were swimming along nicely. I was adjusting nicely to my new life/city, and enjoyed being important in his life, knowing I could always depend on him. We were closer than ever.  Probably too close. Out of the blue, he decided we were too close, we had both developed "feelings" for each other, a romantic relationship would never work out, and therefore, we needed to step back. He said we'd basically been in a relationship, without the sex. He told me he loved me more than anything or anyone in this world. Then he said I was the perfect woman for him... except he wasn't attracted to me. I'm a size 18, he's a marathon runner health nut. I always knew he wasn't attracted to me. R. said he wanted "better for himself than me, and better for me than what we had".

We didn't talk for a while. I argued my point to him-- that people spend their lives looking for a great relationship full of respect, love and laughter like we had.

Yeah, so it wasn't romantic. But we could still be friends. He agreed that he had overreacted and we've spent the last few months trying to be friends. Its not really worked. Things got weird, and I realized that he hurt my feeling more than I wanted to admit so I pulled away without any fanfare-- both the attraction issue but also the way he was willing to cut everything off so brashly. He's stubborn and arrogant sometimes. We've barely spoken the last 6 weeks. Last week, we talked about some work stuff and then, a couple days later, he asked my weekend plans and asked if I wanted to go on a road trip (my favorite thing!).

We have a great time sightseeing and wind up back in the hotel room drinking cheap wine and catching up. We start talking about dating and my life and how I'm happy with where it is. Then he says he wants us to have a child together.  He says he loves me so, so much, he wants to share this really special, intimate thing with me. In his mind, choosing to have a baby with an intelligent, special, wonderful woman he loves is a way bigger compliment than hooking up with some random girl with a tight body he meets in a bar. He doesn't want to live together but he would move to my city.

I'm not sure if he will make a good dad- I know he WANTS to be a good dad but I'm not sure he has the necessary emotional capabilities. I don't know if he wants to be a sperm donor/child support payer, or if he really wants a partnership. I want a partnership. I don't want to be a single mom. I want my kids father to be there at least somewhat-- to take trips with us, to do things together, even if he and I are not romantically involved. I'm not sure what he wants, or, regardless of his intentions, whether he would be able to give me that.

We both work as child support attorneys-- every day, we see people who weren't prepared for a child to come and the results are upsetting. His idea is that those people have children and barely think about the consequences-- why should we, as two people who want to be parents, be hampered by the fact that there is no attraction between us, when we know we'd make great parents for a special kid.

I've always joked that he and I are "entangled". And we are-- we are like a couple in every single way. I know things about him that no other person knows, and I know how to handle him. Its really like what I imagined being in a loving relationship would be, at least on my end. I'm sensitive and tend to give a lot of myself -- except he doesn't always met my emotional needs, mostly because he doesn't really know what they are or how to fulfill them, even in a friendship. I also know he isn't what I really want in a partner. We have very different morals, religious beliefs, values, etc. Spending time away from him helped me realize that here recently.

So, I'm left feeling confused, frustrated and scared. Am I right to be concerned about our strange emotional/romantic history? Am I silly to think I still want some guy to want to have a baby with me because I am fantastic, smart, fun, beautiful AND he's attracted to me? Will I regret this if I don't do it and then never get married or have children/step children? Am I just cowering about the unknown and afraid to step out and make a change into my (admittedly) boring life?


Wow, that’s one long read you just dumped on my lap, but T it’s the last paragraph where we’re going to address the real answers to your problems. I know you know all the answers to them too - you’re just being too pussy to answer them. So let me do it for you.....

Ummm yes you should absolutely be concerned about your strange emotional/romantic history. I mean, as of 6 weeks ago you weren’t talking to the dude. Look, I know you guys have a deep connection, but there’s no denying his constant push and pull pattern with you. He hasn’t even come close to proving that he can back a long term commitment as a friend let alone being there forever as a partner and a father. Also remember the time you said this?

“We have very different morals, religious beliefs, values.”

That alone is one big ass red flag.

Next, NO! Please don’t sell yourself short. Just because you’re 35 and haven’t found someone doesn’t mean you’re some expired piece of meat. F-ck that. Keep putting yourself out there and don’t sacrifice any of the qualities you are looking for in another person. I know this is a weird place to be right now – loving your full life, yet still yearning for what’s missing - but trust me, settling in a relationship is the loneliest feeling you’ll ever know.

Homie, if you’re worried now about getting married as a single free agent, how about trying to meet someone when your tits are lactating, you haven’t slept in literally months, and oh yeah, there’s this guy you procreated with that you’ll never ever be able to get rid of. It’s not the easiest sell....just saying.

Finally, if you feel like life is boring then yes, I’m all for you jumping out of your comfort zone. But like, instead of a baby, how about some baby steps? I.e., take up a new hobby, meet new friends, go out more.

Listen, I’m not opposed to you guys having on-going conversations about this, but for the love of god do not do this any time soon. I don’t think he’s proven to you that he’s ready and frankly, you don’t seem to be either. Most importantly, please put this potential unborn child first in all of this. This decision can’t be made because you two are both in nowhere-land are looking for meaning in life. You know? If it is to happen it's because you are both selfless and responsible enough to give love, and share love.

Thanks for writing in and keep your questions coming to me at [email protected].